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Product Details of [ 186517-01-1 ]

CAS No. :186517-01-1 MDL No. :MFCD08276341
Formula : C14H8Br2 Boiling Point : -
Linear Structure Formula :- InChI Key :BPRGLVVFWRNXEP-UHFFFAOYSA-N
M.W : 336.02 Pubchem ID :22058906
Synonyms :

Safety of [ 186517-01-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 186517-01-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 186517-01-1 ]

[ 186517-01-1 ] Synthesis Path-Downstream   1~84

  • 1
  • [ 108-31-6 ]
  • [ 186517-01-1 ]
  • C18H12Br2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In xylene at 132℃; for 18h;
  • 2
  • 2,6-Dibromo-9,10-dihydro-anthracene-9,10-diol [ No CAS ]
  • [ 186517-01-1 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; sodium tetrahydroborate 1.) 90 deg C, 6 h, 2.) i-PrOH; Yield given. Multistep reaction;
With hydrogenchloride; sodium tetrahydroborate In isopropyl alcohol
  • 3
  • [ 2777-66-4 ]
  • [ 186517-01-1 ]
  • [ 313692-34-1 ]
YieldReaction ConditionsOperation in experiment
70% With copper(l) iodide; diethylamine for 4h; Heating;
  • 4
  • (1s,5s)-9-hexyl-9-borabicyclo[3.3.1]nonane [ No CAS ]
  • [ 186517-01-1 ]
  • 2-bromo-6-hexylanthracene [ No CAS ]
  • 2,6-dihexylanthracene [ No CAS ]
YieldReaction ConditionsOperation in experiment
30% With potassium phosphate In tetrahydrofuran Heating;
  • 5
  • [ 186517-01-1 ]
  • [ 676578-20-4 ]
  • [2,2';6',2'']teranthracene [ No CAS ]
  • 6
  • [ 186517-01-1 ]
  • 2-(6-hexyl-anthracen-2-yl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane [ No CAS ]
  • 6,6''-dihexyl-[2,2';6',2'']teranthracene [ No CAS ]
YieldReaction ConditionsOperation in experiment
14% With sodium carbonate In water; toluene Heating;
  • 7
  • [ 186517-01-1 ]
  • [ 73183-34-3 ]
  • [ 849138-20-1 ]
YieldReaction ConditionsOperation in experiment
99% With potassium phosphate; 2-dicyclohexylphosphino-2’,6’-dimethoxybiphenyl; palladium diacetate In 1,4-dioxane at 70℃; for 20h; Inert atmosphere; Sealed tube;
78% With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In 1,4-dioxane at 85℃; for 22h; Inert atmosphere; 2,6-Dibromoanthracene and bis(pinacolato)diboron were reacted at 85 ° C for twenty-two hours using palladium acetate as a catalyst, 2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl as a ligand, potassium phosphate as a base, 1,4-Dioxane is used as a solvent . The crude product was filtered through a short silica gel column, and the system of ethyl acetate and methylene chloride was applied to a short column of silica gel. The obtained filtrate was spin dried, ultrasonicated with petroleum ether for fifteen minutes, the suspension was filtered, and the obtained solid was air-dried to obtain the compound of formula 2 with a yield of 78%.
76% With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In 1,4-dioxane at 85℃; for 24h; Using 2,6-dibromoanthracene with palladium acetate as a catalyst and 2-dicyclohexylphosphine-2 ', 6'-dimethoxybiphenyl as a ligand,Potassium phosphate as base, dioxane as solvent, and Maura Borylation Reaction at 85 ° C for one day.The crude product was washed with hot petroleum ether to obtain the compound of Formula 2, with a reaction yield of 76%.
73% With potassium acetate In 1,4-dioxane at 110℃; for 15h; Inert atmosphere; 13.A To a solution of 400 mg (1.49 mmol) of 2,6-Dibromo-anthracene (13a) in 1,4- dioxane (30 mL) was added bis-pinacol borate (3.28 mmol), Pd(dppf)Cl2 (0.075 mmol) and KOAc (8.94 mmol). The reaction mixture was put under N2 atmosphere,then heated to 110 0C and allowed to stir at this temperature for about 15 hours. The reaction mixture was then cooled to room temperature and concentrated in vacuo. The resulting residue was purified using column chromatography on silica gel (gradient elution using petroleum etheϖEtOAc from 50: 1 to 10: 1) to provide Compound 13b (467 mg, 73% yield).
73% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 110℃; for 15h;
71% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 20 - 80℃; for 20.5h; Inert atmosphere;
48% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In dimethyl sulfoxide at 80℃; for 16h;
48% With potassium acetate In dimethyl sulfoxide at 80℃; for 16h; 5 A nitrogen- flushed round bottom flask was charged with 2,6-dibromoanthracene (prepared as in Example 1 , 21.73 g, 64.67 mmol), bis(pinacolato)diboron (41.06 g, 161.67 mmol), potassium acetate (25.90 g, 263.85 mmol) and [1 ,1'-bis(diphenylphosphino)ferrocene]-dichloropalladium complex with dichloromethane (1 :1 ) (1.64 g, 2.0 mmol). Dimethyl sulfoxide (DMSO, 300 ml) was then added and the mixture was bubbled with nitrogen for 15 min. After heating at 80 0C for 16 h, the reaction mixture was cooled to room temperature and poured into ice-water (600 ml). It was then extracted with methylene chloride (2x) and the combined organic layer was dried over anhydrous magnesium sulfate. The solvent was removed by rotary evaporation and the residue was purified several times by flash silica gel column with chloroform/hexane (1 :2 to 1 :1 to 2:1 to chloroform) as eluent to give 13.4698 g of (48%) bright yellow fine crystals, mp: >260 0C. 1H NMR (CDCI3, 500 MHz): δ 8.56 ppm (s, 2 H), 8.44 ppm (s, 2 H), 7.99-7.97 ppm (d, 2 H, J = 8.5 Hz), 7.79-7.77 ppm (d, 2 H1 J = 8.5 Hz ), δ 1.41 ppm (s, 24 H); 13C-NMR (CDCI3, 500 MHz): δ 137.7, 133.1 , 132.2, 129.5, 127.8, 127.5, 84.37, 25.33 ppm. El, MS m/z (%): 430 (100, M+). Anal. Found: C, 71.76; H, 7.32; B, 4.89
38% With potassium acetate In dimethyl sulfoxide at 80℃; Inert atmosphere; AA1 A mixture of 2,6- dibromoanthracene (500 mg, 1.49 mmol), bis(pinacolato)diboron (756 mg, 2.98 mmol)and KOAc (585 mg, 5.96 mmol) in DMSO (10 mL) was degassed with N2 gas for 20 minutes. To the degassed solution was added PdCl2(dppf) (55 mg, 0.075 mmol) then the reaction was heated to 8O°C overnight. After cooling to room temperature, the reaction was poured into H2O and extracted with CH2Cl2. The organic phase was collected then washed with H2O and brine. After drying over Na2Sθ4, the organic phase was concentrated then purified by silica gel chromatography (30-100% CH2Cl2-hexanes gradient) to afford 2,6-anthracene-bis-4,4,5,5- tetramethyl-1,3,2-dioxaborolane (241 mg, 0.56 mmol, 38% yield). 1H-NMR: 400 MHz, (DMSO-d6) δ: 8.57 (s, 2H), 8.46 (s, 2H), 8.00 (d, 2H), 7.79 (d, 2H).
With potassium acetate
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In 1,4-dioxane at 80℃; for 20h; Inert atmosphere;
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate at 80℃; 1.1 Step 1 : A Miyaura borylation reaction can be used to form (a). 2,6- dibromoanthracene can be reacted with bis(pinacolato)diboron in the presence of KOAc and PdCl2(dppf) catalyst in a solvent such as dioxane or DMSO at a temperature of 80°C. The product (a) can be isolated by conventional techniques.

Reference: [1]Huang, Ze-Ao; Chen, Chen; Yang, Xiao-Di; Fan, Xiang-Bing; Zhou, Wen; Tung, Chen-Ho; Wu, Li-Zhu; Cong, Huan [Journal of the American Chemical Society, 2016, vol. 138, # 35, p. 11144 - 11147]
[2]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES; Technical Institute of Physics & Chemistry(in: CAS) - CN108586187, 2018, A Location in patent: Paragraph 0032; 0033
[3]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES; Technical Institute of Physics & Chemistry(in: CAS) - CN110272332, 2019, A Location in patent: Paragraph 0036-0037; 0052
[4]Current Patent Assignee: MERCK & CO INC - WO2010/132538, 2010, A1 Location in patent: Page/Page column 110
[5]Yu, Wensheng; Coburn, Craig A.; Yang, De-Yi; Meinke, Peter T.; Wong, Michael; Rosenblum, Stuart B.; Chen, Kevin X.; Njoroge, George F.; Chen, Lei; Dwyer, Michael P.; Jiang, Yueheng; Nair, Anilkumar G.; Selyutin, Oleg; Tong, Ling; Zeng, Qingbei; Zhong, Bin; Ji, Tao; Hu, Bin; Agrawal, Sony; Xia, Ellen; Zhai, Ying; Liu, Rong; Kong, Rong; Ingravallo, Paul; Asante-Appiah, Ernest; Nomeir, Amin; Fells, James; Kozlowski, Joseph A. [Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 13, p. 3158 - 3162]
[6]Sonar, Prashant; Singh, Samarendra P.; Williams, Evan L.; Li, Yuning; Soh, Mui Siang; Dodabalapur, Ananth [Journal of Materials Chemistry, 2012, vol. 22, # 10, p. 4425 - 4435]
[7]Meng, Hong; Sun, Fangping; Goldfinger, Marc B.; Jaycox, Gary D.; Li, Zhigang; Marshall, Will J.; Blackman, Gregory S. [Journal of the American Chemical Society, 2005, vol. 127, # 8, p. 2406 - 2407]
[8]Current Patent Assignee: DUPONT DE NEMOURS INC - WO2006/50496, 2006, A1 Location in patent: Page/Page column 40
[9]Current Patent Assignee: GILEAD SCIENCES INC - WO2010/132601, 2010, A1 Location in patent: Page/Page column 458
[10]Zhao, Yang; Yan, Lijia; Murtaza, Imran; Liang, Xiao; Meng, Hong; Huang, Wei [Organic electronics, 2017, vol. 43, p. 105 - 111]
[11]Xu, Wei; Yang, Xiao-Di; Fan, Xiang-Bing; Wang, Xin; Tung, Chen-Ho; Wu, Li-Zhu; Cong, Huan [Angewandte Chemie - International Edition, 2019, vol. 58, # 12, p. 3943 - 3947][Angew. Chem., 2019, vol. 131, # 12, p. 3983 - 3987,5]
[12]Current Patent Assignee: DUPONT DE NEMOURS INC - WO2020/33480, 2020, A1 Location in patent: Page/Page column 77
  • 8
  • [ 872-36-6 ]
  • [ 186517-01-1 ]
  • 2,6-dibromo-9,10-dihydro-9,10-ethanoanthracene-cis-11,12-diyl carbonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% In xylene at 180℃; for 72h;
  • 9
  • [ 46710-42-3 ]
  • [ 186517-01-1 ]
  • 10
  • 2-[2-(4-pentylphenyl)vinyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]
  • [ 186517-01-1 ]
  • 2,6-bis-[2-(4-pentyl-phenyl)-vinyl]-anthracene [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With sodium carbonate In water; toluene at 90℃; for 72h;
  • 11
  • [ 115-19-5 ]
  • [ 186517-01-1 ]
  • C24H22O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; copper(I) bromide; lithium bromide In tetrahydrofuran at 85 - 90℃; for 2h;
  • 13
  • [ 633-70-5 ]
  • [ 186517-01-1 ]
YieldReaction ConditionsOperation in experiment
53% With hydrogen bromide; hypophosphorous acid; acetic acid; at 140℃; 3 g of 2,6-DBAQ (8.2 mmol), 170 ml of AcOH, 20 mlof HBr and 15 ml of H3PO2 were sequentially added to around flask and refluxed at 140 C. After 5 days of reaction,the solution was washed and filtered using ice waterand ethanol to obtain 1.46 g of solid (yield: 53%).1H-NMR (300 MHz, CDCl3, ): 8.31 (s, 2H), 8.18(s, 2H), 7.90 (d, 2H), 7.56 (d, 2H).
50% With hydrogen iodide; hypophosphorous acid; In acetic acid; at 150℃; for 96h; Compound (6) (<strong>[633-70-5]2,6-dibromoanthraquinone</strong>) (15 g, 40.98 mmol) obtained as above, 600 ml of glacial acetic acid, 105 ml of HI and 60 ml of H3PO2 were charged in a reactor, and the mixture was heated under reflux at 150C for 4 days. After washing with water and ethanol, the mixture was extracted with toluene by means of a Soxhlet device to obtain yellowish green solid (6.9 g, 50%) .1H NMR (300 MHz, CDCl3, ppm) : 8.31 (s, 2H), 8.18 (s, 2H), 7.90 (d, 2H) , 7.56 (d, 2H).
With sodium hydroxide; In chloroform; water; (2) Synthesis of 2,6-dibromoanthracene 30 g of <strong>[633-70-5]2,6-dibromoanthraquinone</strong>, 5 g of Zn and 25 g of NaOH were stirred in 200 mL of water at 100C for 24 hours and when the reaction was complete, the reaction materials were filtered. The thus-obtained organic material and inorganic material were dissolved in chloroform and the resulting mixture was re-filtered. The obtained filtrate was applied to a silica gel short column, thereby separating the inorganic material. The separated material was recrystallized from MC and MeOH, thereby obtaining 15 g of 2,6-dibromoanthracene.
With hydrogen iodide; hypophosphorous acid; In water; acetic acid; for 120h;Heating / reflux; This example illustrates the synthesis of an exemplary compound (Compound 7). It will be apparent to one skilled in the art that other compounds represented by Formulas 1 or 2 can be synthesized in a manner similar to that described in Example 1; A 500 imL 3-neck round-bottomed flask was charged with anhydrous copper bromide (CuBr2) (56 g, 0.25 mol), f-foutyl nitrite (90 %, 34 g, 0.30 mol) and anhydrous acetonitrile (300 ml_). The mixture was then refluxed at 650C for 10 minutes. Thereafter, 2,6- diaminoanthra-quinone (Compound 22, 23.8 g, 0.10 mol) was slowly added over period of 30 minutes.When gas evolution ceased, the reaction mixture was cooled to room temperature and poured into 6 M HCI (500 mL). The precipitate was filtered and washed with water and ethanol. The crude product was then purified by sublimation (~270 0C /60 mTorr) to give 33.62 g (92%) of purified product. The product had a mp>280 0C. The product was identified as <strong>[633-70-5]2,6-dibromoanthraquinone</strong> (Compound 23); Subsequently, a mixture of <strong>[633-70-5]2,6-dibromoanthraquinone</strong> (22.41 g, 61.23 mmol), acetic acid (250 rnL), 56-58% hydriodic acid (100 mL), and 50% hypophosphorous acid (55 mL) was refluxed for 5 days. The mixture was then cooled to room temperature and poured into ice water (800 mL). Thereafter, the precipitate was filtered and washed with water and ethanol. The precipitate was then re-crystallized from toluene (620 mL) to give14.49 g of pale yellow flake-like crystals of 2,6- dibromoanthracene (Compound 24); A solution of 2,6-dibromoanthracene (1.68 g, 5.0 mmol) and 2- benzo[b]thiophen-2-yl-[1 ,3,2]dioxaborinane (3.27 g, 15 mmol) dissolved in toluene (80 ml) was prepared . Sodium carbonate (2.12 g, 20 mmol) dissolved in water (10 ml) was added to this solution. Subsequently, a phase-transfer agent, Aliquat 336 (0.8 g, 2.0 mmol) was added to the solution. The mixture was bubbled with nitrogen for 15 minutes. Thereafter, tetrakis(triphenylphosphine)palladium(0) (110 mg, 2 % mol) was added. The mixture was heated to 90 0C for three days under a nitrogen atmosphere. The reaction mixture was then cooled to room temperature and poured into methanol (600 ml). The yellow precipitate was filtered off, washed with water, dilute acid (5 % HCI), methanol, and then with acetone three times to remove the starting material and the mono-substituted by-product.The crude product was purified by sublimation (270 C/60 mtorr) in a 3-zone furnace. Finally, the purified product was recrystallized from EPO <DP n="36"/>mixed xylene isomers containing ortho-, para- and meta-xylene isomers (Aldrich, Cat. 32057-9) to give 1.49 g (67 %) of bright yellow crystals of 2,6-anthracene-bis-2'-benzothiophene (Compound 7).

  • 14
  • [ 186517-01-1 ]
  • 2,6-dianthryl-9,10-dihydro-9,10-ethanoanthracene-11,12-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 72 percent / xylene / 72 h / 180 °C 2: 25 percent / aq. Na2CO3 / [Pd(PPh3)4] / toluene / 18 h / Heating 3: aq. NaOH / dioxane / 1 h / Heating 4: 0.046 g / trifluoroacetic anhydride; DMSO / CH2Cl2 / -60 - 20 °C
  • 15
  • [ 186517-01-1 ]
  • C44H30O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 72 percent / xylene / 72 h / 180 °C 2: 25 percent / aq. Na2CO3 / [Pd(PPh3)4] / toluene / 18 h / Heating 3: aq. NaOH / dioxane / 1 h / Heating
  • 16
  • [ 186517-01-1 ]
  • 2,6-(2'-anthryl)-9,10-dihydro-9,10-ethanoanthracene-cis-11,12-diyl carbonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 72 percent / xylene / 72 h / 180 °C 2: 25 percent / aq. Na2CO3 / [Pd(PPh3)4] / toluene / 18 h / Heating
  • 17
  • [ 186517-01-1 ]
  • dimethyl 11,11'-(anthracene-2,6-diyl)bis[undecanoate] [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 70 percent / Et2NH; CuI / [Pd(Ph3P)2Cl2] / 4 h / Heating 2: 55 percent / activated Raney-Ni / tetrahydrofuran / 1 h / 20 °C
  • 18
  • [ 131-14-6 ]
  • sulfur [ No CAS ]
  • [ 186517-01-1 ]
  • 19
  • [ 186517-01-1 ]
  • C19H16Br2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: xylene / 18 h / 132 °C 2: 16 h / 56 °C
  • 20
  • [ 186517-01-1 ]
  • C20H18Br2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: xylene / 18 h / 132 °C 2: 16 h / 56 °C 3: diethyl ether / 20 °C
  • 21
  • [ 162717-58-0 ]
  • [ 186517-01-1 ]
  • 2,6-bis(2,2'-bithien-5-yl)-anthracene [ No CAS ]
YieldReaction ConditionsOperation in experiment
46% In DMF (N,N-dimethyl-formamide) at 90℃; for 20.3333h; 5 A reaction vessel was charged with Pd (PPh3) 4 (70 mg, 0.061 mmol, 1.3 mol%), 2,6-dibromoanthracene (800 mg, 2.38 mmol), DMF (20 mL), and 5-tri-n-butylstannyl- 2, 2'-bithiophene (2.17 g, 4.77 mmol). The mixture was bubbled through with N2 for 20 min and then stirred for 20 h at 90 °C. After cooling, the suspended solid was isolated on a glass filter frit (10-20 μm pores), washed with acetone (20 mL), water (50 mL), and air dried overnight. Gradient sublimation of the crude powder at a source temperature of 275- 350 °C afforded 550 mg (46%) of bright orange product. EIMS : 506 ([M]+, 100%), 253 ([M]2+, 30%). UV-vis (saturated CHCl3) : λmax,/NM (absorbance), 348 (0.12), 418 (0.06), 440 (0.06, sh), 519 (0.009). Fluorescence (CHCL3), λMAX/NM (relative intensity: 469 (1.0), 495 (0.69 sh). DSC: peak temperature (ΔH), 360 °C (131 J/g). Anal. Calcd. for C30H18S4 : C, 71. 1; H, 3.58 ; S, 25.3. Found :, C, 70.5 ; H, 3.52 ; S, 25.2.
  • 22
  • [ 885622-94-6 ]
  • [ 186517-01-1 ]
  • 2,6-anthracene-bis-2'-benzothiophene [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With sodium carbonate In water; toluene at 90℃; for 72h; 1 This example illustrates the synthesis of an exemplary compound (Compound 7). It will be apparent to one skilled in the art that other compounds represented by Formulas 1 or 2 can be synthesized in a manner similar to that described in Example 1; A 500 imL 3-neck round-bottomed flask was charged with anhydrous copper bromide (CuBr2) (56 g, 0.25 mol), f-foutyl nitrite (90 %, 34 g, 0.30 mol) and anhydrous acetonitrile (300 ml_). The mixture was then refluxed at 650C for 10 minutes. Thereafter, 2,6- diaminoanthra-quinone (Compound 22, 23.8 g, 0.10 mol) was slowly added over period of 30 minutes.When gas evolution ceased, the reaction mixture was cooled to room temperature and poured into 6 M HCI (500 mL). The precipitate was filtered and washed with water and ethanol. The crude product was then purified by sublimation (~270 0C /60 mTorr) to give 33.62 g (92%) of purified product. The product had a mp>280 0C. The product was identified as 2,6-dibromoanthraquinone (Compound 23); Subsequently, a mixture of 2,6-dibromoanthraquinone (22.41 g, 61.23 mmol), acetic acid (250 rnL), 56-58% hydriodic acid (100 mL), and 50% hypophosphorous acid (55 mL) was refluxed for 5 days. The mixture was then cooled to room temperature and poured into ice water (800 mL). Thereafter, the precipitate was filtered and washed with water and ethanol. The precipitate was then re-crystallized from toluene (620 mL) to give14.49 g of pale yellow flake-like crystals of 2,6- dibromoanthracene (Compound 24); A solution of 2,6-dibromoanthracene (1.68 g, 5.0 mmol) and 2- benzo[b]thiophen-2-yl-[1 ,3,2]dioxaborinane (3.27 g, 15 mmol) dissolved in toluene (80 ml) was prepared . Sodium carbonate (2.12 g, 20 mmol) dissolved in water (10 ml) was added to this solution. Subsequently, a phase-transfer agent, Aliquat 336 (0.8 g, 2.0 mmol) was added to the solution. The mixture was bubbled with nitrogen for 15 minutes. Thereafter, tetrakis(triphenylphosphine)palladium(0) (110 mg, 2 % mol) was added. The mixture was heated to 90 0C for three days under a nitrogen atmosphere. The reaction mixture was then cooled to room temperature and poured into methanol (600 ml). The yellow precipitate was filtered off, washed with water, dilute acid (5 % HCI), methanol, and then with acetone three times to remove the starting material and the mono-substituted by-product.The crude product was purified by sublimation (270 °C/60 mtorr) in a 3-zone furnace. Finally, the purified product was recrystallized from EPO mixed xylene isomers containing ortho-, para- and meta-xylene isomers (Aldrich, Cat. 32057-9) to give 1.49 g (67 %) of bright yellow crystals of 2,6-anthracene-bis-2'-benzothiophene (Compound 7).
  • 23
  • [ 885622-95-7 ]
  • [ 186517-01-1 ]
  • 2,6-bis(4-methylthiophen-2-yl)anthracene [ No CAS ]
YieldReaction ConditionsOperation in experiment
26% With sodium carbonate In water; toluene at 90℃; for 72h; 2 Bis-(4'-methyl-thiophen-2'yl)-2,6-anthracene: To a mixture of 2,6- dibromoanthracene (prepared as in Example 1 , 3.36 g, 10.0 mmol) and 2- (4-methyl-thiophen-2-yl)-[1 ,3,2]dioxaborinane (5.46 g, 30mmol) in toluene (150 ml) was added Na2CO3 (5.30 g, 50 mmol) dissolved in water (25 ml), followed by the addition of phase-transfer agent Aliquat 336 (2 g, 5 mmol). The mixture was bubbled with nitrogen for 15 min. Then, tetrakis(triphenylphosphine)palladium(0) (232 mg, 2 % mol) was added. The mixture was heated to 90 0C for three days under a nitrogen atmosphere. The reaction mixture was cooled to room temperature and poured into methanol (300 ml). The yellow precipitate was filtered off, washed with water, dilute acid (5 % HCI), water, methanol, then with acetone (3x) to remove the starting material and the mono-substituted by¬ product. The crude product was purified in a 3-zone furnace sublimation and then by recrystallization from xylenes to give 0.97 g (26%) of bright yellow product. El, MS m/z (%): 370 (100, M+).
  • 24
  • [ 885622-96-8 ]
  • [ 186517-01-1 ]
  • 2,6-bis(4-butyllthiophen-2-yl)anthracene [ No CAS ]
YieldReaction ConditionsOperation in experiment
25% With sodium carbonate In water; toluene at 90℃; for 72h; 3 Bis-(4'-butyl-thiophen-2'vO-2,6-anthracene: To a mixture of 2,6- dibromoanthracene (prepared as described in Example 1 , 2.016 g, 6.0 mmol) and 2-(4-butyl-thiophen-2-yl)-[1 ,3,2]dioxaborinane (4.034 g, 18.0 mmol) in toluene (90 ml) was added Na2CO3 (3.18 g, 30 mmol) dissolved in water (15 ml), followed by the addition of phase-transfer agent Aliquat 336 (1.2 g, 3.0 mmol). The mixture was bubbled with nitrogen for 15 min. Then, tetrakis(triphenylphosphine)palladium(0) (139 mg, 2 % mol) was added. The mixture was heated to 90 0C for three days under a nitrogen atmosphere. The reaction mixture was cooled to room temperature and poured into methanol (300 ml). The yellow precipitate was filtered off, washed with water, dilute acid (5 % HCI), water, methanol, then with EPO acetone (3x) to remove the starting material and mono-substituted by¬ product. The crude product was purified by 3-zone furnace sublimation and finally by recrystallization from xylenes to give 0.68 g (25%) of briglht yellow product. 1H NMR (CDC/3-d3, 500 MHz): δ 8.34 ppm (s, 2 H), 8.1-4 ppm (s, 2 H), 7.97-7.95 ppm (d, 2 H, J = 8.5 Hz), 7.72-7.70 ppm (d, 2 HI , J = 8.5 Hz ), 7.31 ppm (s, 2 H), 6.92 ppm (s, 2 H), 2.65-2.68 ppm (t, 4 H, J = 8.6 Hz), 1.68 ppm (m, 4 H), 1.45 ppm (m, 4 H), 0.89 ppm (t, 6 H, J = 7.5 Hz); 13C-NMR (CDCI3, 500 MHz): δ 144.8, 144.5, 132.3, 132.0, 131.9, 131.8, 129.0, 126.6, 125.4, 125.0, 124.0, 120.3, 33.01 , 30.74, 22.76, 14.19 ppm. El, MS m/z (%): 454 (100, M+); HRMS found: 454.1776. Ca eld, C30H30S2: 454.1789. Anal., Found: C, 79.55; H, 6.74; S, 14.56.
  • 25
  • [ 885622-98-0 ]
  • [ 186517-01-1 ]
  • 2,6-bis(4-hexylthiophen-2-yl)anthracene [ No CAS ]
YieldReaction ConditionsOperation in experiment
21% With sodium carbonate In water; toluene at 90℃; for 72h; 4 Bis-(4'-hexyl-thiophen-2'vD-2,6-anthracene: To a mixture of 2,6- dibromoanthracene (prepared as described in Example 1 , 1.5829 g, 4.71 mmol) and 2-(4-hexyl-thiophen-2-yl)-[1 ,3,2]dioxaborinane (2.82 g, 11.18 mmol) in toluene (75 ml) was added Na2CO3 (2.12 g, 20 mmol) dissolved in water (10 ml) followed by the addition of phase-transfer agent Aliquat 336 (1.0 g, 2.5 mmol). The mixture was bubbled with nitrogen for 15 min. Then, tetrakis(triphenylphosphine)palladium(0) (110 mg, 2 % mol) was added. The mixture was heated to 90 0C for three days under a nitrogen atmosphere. The reaction mixture was cooled to room temperature and poured into methanol (300 ml). The yellow precipitate was filtered off, washed with water, dilute acid (5 % HCI), water, methanol, then with acetone (3x) to remove the starting material and mono-substituted by¬ product. The crude product was purified by 3-zone furnace sublimation and finally by recrystallization from xylenes to give 0.50 g (21 %) of bright yellow product. 1H NMR (CDC/3-d3, 500 MHz): δ 8.35 ppm (s, 2 H), 8.15 ppm (s, 2 H), 7.82-7.95 ppm (d, 2 H, J = 8.5 Hz), 7.71-7.79 ppm (d, 2 H, J = 8.5 Hz ), 7.32 ppm (s, 2 H), 6.92 ppm (s, 2 H), 2.60-2.67 ppm (t, 4 H, J = 8.6 Hz), 1.71 ppm (m, 4 H), 1.33-1.43 ppm (m, 12 H), 0.89 ppm (t, 6 H, J = 7.5 Hz); 13C-NMR (CDCI3, 500 MHz): δ 145.6, 143.7, 132.7, 132.3, 131.2, 130.0, EPO 129.8, 126.7, 125.8, 125.0, 124.1 , 32.46, 32.38, 31.31 , 29.54, 23.36, 14.53 ppm. El, MS m/z (%): 510 (100, M+); HRMS found: 510.2416. Analysis, Found: C, 80.30; H, 7.74; S, 12.84.
  • 26
  • [ 536-74-3 ]
  • [ 186517-01-1 ]
  • [ 1019925-43-9 ]
YieldReaction ConditionsOperation in experiment
71.3% With copper(l) iodide; triethylamine In toluene for 18h; Heating / reflux; 1 Compound (7) (3 g, 9 mmol) obtained from Preparation Example 4, phenylacetylene (0.312 g, 2 mmol), CuI(I) (1.151 g, 2 mmol) and Pd(pph3)2Cl2 (6 mol%) were added to dry toluene (30 mL) and dry triethylamine (30 mL) , and the mixture was heated under reflux for 18 hours. The reaction temperature was lowered to room temperature, and the volatile substances were removed by using a rotary evaporator. After washing with dichloromethane, the solid was extracted with toluene by using a Soxhlet device to obtain yellowish green solid (2.41 g, 71.3%) .
  • 27
  • [ 156641-98-4 ]
  • [ 186517-01-1 ]
  • [ 1065644-45-2 ]
YieldReaction ConditionsOperation in experiment
40% To 100 mL of THF and 2M aqueous solution of K2CO3, added were 2,6-dibromo-9, 10-dihydroanthracene (Compound 15) (5 g, 0.015 mol) obtained from Preparation Example 11 and 6- methoxynaphthalen-2-yl-2-boronic acid (Compound 18) (14.9 g, 0.033 mol) obtained from Preparation Example 13, and the mixture was stirred under nitrogen atmosphere for 30 minutes. After adding tetrakis (triphenylphosphine-palladium) (0.5 g, 0.4 mmol) , the resultant mixture was stirred at 85-95 C for about 24 hours . Then the reaction was quenched by pouring the mixture to 2N-HC1. The precipitate produced was filtered, and extracted with toluene by using a Soxhlet device. Recrystallization from chlorobenzene gave the desired compound(110) (yield: 40%) .FT-IR (KBr, cm-1): 2955, 2889 (aliphatic C-H), 3008 cm-1(aromatic C=C) , 1240 cm-1 (Ar-C-O).
  • 28
  • [ 79887-11-9 ]
  • [ 186517-01-1 ]
  • [ 1065644-37-2 ]
YieldReaction ConditionsOperation in experiment
50% With copper(l) iodide; palladium bis[bis(diphenylphosphino)ferrocene] dichloride; diisopropylamine; triphenylphosphine at 90℃; for 16h; Inert atmosphere;
50% With copper(l) iodide; diisopropylamine In toluene for 16h; Heating / reflux; 2 Compound (7) (1 g, 2.98 mmol) obtained from Example 4 was added to dry i-Pr2NH (15 mL) and dry toluene (15 mL) . To the mixture, added were Compound (5) (5.96 mmol) obtained from Preparation Example 3, Pd(dppf)Cl2 (6 mol%) and CuI (34 mg, 0.18 mmol), and the resultant mixture was heated under reflux for 16 hours. The reaction temperature was lowered to room temperature, and the precipitate was filtered. The precipitate was washed with toluene, and purified with toluene by using a Soxhlet device .Compound (102) : Light yellow solid, 1H NMR (CDCl3, 300 MHz): δ 8.37 ppm (s, 2H), 8.21 ppm (s, 2H), 7.99-7.97 ppm (d, 2H, J=8.64 Hz), 7.57-7.52 ppm (m, 6H), 7.28-7.20 ppm (d, 4H, J=7.44 Hz), 2.68-2.63 ppm (t, 4H, J=7.13 Hz), 1.65 ppm (m, 4H), 1.34 ppm (m, 12H), 0.91 ppm (m, 6H).
  • 29
  • [ 1244370-25-9 ]
  • [ 186517-01-1 ]
  • [ 1244370-24-8 ]
YieldReaction ConditionsOperation in experiment
0.16 g With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide; toluene at 90℃; for 30h;
  • 30
  • [ 33513-42-7 ]
  • [ 186517-01-1 ]
  • [ 1262433-90-8 ]
YieldReaction ConditionsOperation in experiment
61% Stage #1: 2,6-dibromoanthracene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;
17% Stage #1: 2,6-dibromoanthracene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1.5h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane at 20℃; Synthesis of Anthracene-2,6-dicarbaldehyde 2,6-dibromoanthracene (0.10 g, 0.30 mmol) was dissolved in dry THF (3 mL) and stirred at -78°C. n-BuLi (1.6 mol dm-3 in hexane, 5 ml) was slowly added for 30 min to the solution and then stirred for further 1 h. Dry DMF (2mL) was added slowly to the reaction mixture and allowed to warm to ambient temperature slowly. The reaction was quenched by pouring the mixture of methanol and water (1:1) into the reaction mixture. The reaction mixture was extracted with water and toluene. The organic phase was evaporated. The resultant solid was recrystallized from the mixture of ethanol and toluene to obtain anthracene-2,6-dicarbaldehyde as yellow solid (17 % yield) .
Stage #1: 2,6-dibromoanthracene With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -78℃; for 1h; 2 To a flame-dried two-necked flask, 2,6-dibromoanthracene (0.34 g, 1 mmol) was added, and thereafter, the inside of the container was filled with argon gas. Anhydrous tetrahydrofuran (15 mL) was added to the flask, and the mixed solution was then cooled to -78° C. To the reaction solution, n-butyllithium (n-BuLi, 21.4 mL, 34.2 mmol) was slowly added dropwise, and the obtained mixture was then stirred at -78° C. for 1 hour. Thereafter, anhydrous dimethylformamide (DMF) was slowly added dropwise to the reaction solution, and the obtained mixture was then stirred for 1 hour. Thereafter, the temperature was slowly increased to room temperature, and water was then added to the reaction solution for quenching. The resultant was extracted with toluene, and the organic layer was then washed with water. After that, magnesium sulfate (anhydrous) was added to the organic layer, so that the obtained mixture was dried and concentrated. The concentrate was purified by column chromatography (developing solvent=chloroform 9:acetone 1). Thereafter, the resultant was recrystallized from a mixed solvent of toluene/ethanol, to obtain anthracene-2,6-dicarbaldehyde in the form of a yellow solid.
  • 31
  • CH2Cl2-hexanes [ No CAS ]
  • bis(pinacolato)diboron [ No CAS ]
  • PdCl2dppf2 [ No CAS ]
  • [ 186517-01-1 ]
  • [ 849138-20-1 ]
YieldReaction ConditionsOperation in experiment
With potassium acetate In dimethyl sulfoxide 13 Preparation of Compound 13 Example 13 Preparation of Compound 13 2,6-Anthracene-bis-4,4,5,5-tetramethyl-1,3,2-dioxaborolane: A mixture of 2,6-dibromoanthracene (500 mg, 1.49 mmol), bis(pinacolato)diboron (756 mg, 2.98 mmol) and KOAc (585 mg, 5.96 mmol) in DMSO (10 mL) was degassed with N2 gas for 20 minutes. To the degassed solution was added PdCl2dppf2 (55 mg, 0.075 mmol) then the reaction was heated to 80° C. overnight. After cooling to room temperature, the reaction was poured into H2O and extracted with CH2Cl2. The organic phase was collected then washed with H2O and brine. After drying over Na2SO4, the organic phase was concentrated then purified by silica gel chromatography (30-100% CH2Cl2-hexanes gradient) to afford 2,6-anthracene-bis-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (241 mg, 0.56 mmol, 38% yield). 1H-NMR: 400 MHz, (DMSO-d6) δ: 8.57 (s, 2H), 8.46 (s, 2H), 8.00 (d, 2H), 7.79 (d, 2H).
  • 32
  • [ 186517-01-1 ]
  • [ 25015-63-8 ]
  • [ 849138-20-1 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In toluene
  • 33
  • [ 186517-01-1 ]
  • [ 1020110-31-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine / 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) / toluene 2: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / toluene; ethanol; water / 44 h / 76 °C / Inert atmosphere
  • 34
  • [ 115573-46-1 ]
  • [ 186517-01-1 ]
  • [ 1065644-39-4 ]
YieldReaction ConditionsOperation in experiment
27% With copper(l) iodide; palladium bis[bis(diphenylphosphino)ferrocene] dichloride; diisopropylamine; triphenylphosphine at 90℃; Inert atmosphere;
  • 35
  • [ 186517-01-1 ]
  • [ 126708-45-0 ]
  • [ 1065644-38-3 ]
YieldReaction ConditionsOperation in experiment
38% With copper(l) iodide; palladium bis[bis(diphenylphosphino)ferrocene] dichloride; diisopropylamine; triphenylphosphine at 90℃; Inert atmosphere;
  • 36
  • [ 186517-01-1 ]
  • [ 135883-45-3 ]
  • [ 1364344-58-0 ]
YieldReaction ConditionsOperation in experiment
80% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine In tetrahydrofuran for 18h; Reflux;
  • 37
  • [ 1398398-07-6 ]
  • [ 186517-01-1 ]
  • [ 1423167-69-4 ]
YieldReaction ConditionsOperation in experiment
80% With tetrakis(triphenylphosphine) palladium(0); Aliquat 336; sodium carbonate In toluene at 90℃; for 72h; Inert atmosphere;
  • 38
  • [ 1222450-44-3 ]
  • [ 186517-01-1 ]
  • [ 1422514-29-1 ]
YieldReaction ConditionsOperation in experiment
43% With tetrakis(triphenylphosphine) palladium(0); Aliquat 336; sodium carbonate In water; toluene at 90℃; for 72h; Inert atmosphere;
  • 39
  • [ 1401250-76-7 ]
  • [ 186517-01-1 ]
  • [ 594838-54-7 ]
YieldReaction ConditionsOperation in experiment
50% With tetrakis(triphenylphosphine) palladium(0); Aliquat 336; sodium carbonate In water; toluene at 90℃; for 72h; Inert atmosphere;
  • 40
  • 2-(5'-hexyl-[2,2']bithiophenyl-5-yl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane [ No CAS ]
  • [ 186517-01-1 ]
  • 2,6-bis(5'-hexylbithiophen-2'-yl)anthracene [ No CAS ]
YieldReaction ConditionsOperation in experiment
42% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water; toluene at 90℃; for 24h; Inert atmosphere;
  • 41
  • [ 97674-02-7 ]
  • [ 186517-01-1 ]
  • [ 1221682-04-7 ]
YieldReaction ConditionsOperation in experiment
600 mg With bis-triphenylphosphine-palladium(II) chloride In 1,4-dioxane at 100℃; for 16h; Inert atmosphere; B.26.a Example B26, Step a Example B26 Example B26, Step a To a solution of 2,6-dibromoanthracene (1.2 g, 3.57 mmol) in 1,4-dioxane (20 mL) was added 1-ethoxyvinyltri-n-butyltin (3.65 mL, 10.71 mmol) under N2. Then Pd(PPh3)2Cl2 (0.251 g, 0.357 mmol) was added. The reaction mixture was heated at 100° C. for 16 h then cooled to rt and diluted with DCM and 1.5 N HCl. The organic layer was separated and the aqueous layer was extracted with DCM. The combined organic layer was dried over Na2SO4 and concentrated. The crude was purified by Combiflash Isco (Silica gel, 12 g, Redisep, 0.5% MeOH in CHCl3) and the resulting product was washed with petroleum ether to yield 1,1'-(anthracene-2,6-diyl)diethanone (600 mg) as a yellow solid. 1H NMR (CDCl3, δ=7.26 ppm, 400 MHz): δ 8.67 (s, 2H), 8.61 (s, 2H), 8.44-8.04 (m, 4H), 2.78 (s, 6H).
600mg With bis-triphenylphosphine-palladium(II) chloride In 1,4-dioxane at 100℃; for 16h; Inert atmosphere; B26.a To a solution of 2,6-dibromoanthracene (1.2 g, 3.57 mmol) in 1,4-dioxane (20mL) was added 1 -ethoxyvinyltri-n-butyltin (3.65 mL, 10.71 mmol) under N2. ThenPd(PPh3)2C12 (0.251 g, 0.3 57 mmol) was added. The reaction mixture was heated at 100 °C for 16 h then cooled to rt and diluted with DCM and 1.5 N HC1. The organic layer was separated and the aqueous layer was extracted with DCM. The combined organic layer was dried over Na2SO4 and concentrated. The crude was purified byCombiflash Isco (Silica gel,12 g, Redisep, 0.5 % MeOH in CHC13) and the resulting product was washed with petroleum ether to yield 1,1’-(anthracene-2,6- diyl)diethanone (600 mg) as a yellow solid. ‘H NMR (CDC13, ö = 7.26 ppm, 400 MHz): ö 8.67 (s, 2 H), 8.61 (s, 2 H), 8.44-8.04 (m, 4 H), 2.78 (s, 6 H).
  • 42
  • [ 186517-01-1 ]
  • [ 306934-95-2 ]
  • [ 1613546-82-9 ]
YieldReaction ConditionsOperation in experiment
83% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene at 80℃; for 24h; Inert atmosphere;
  • 43
  • [ 97674-02-7 ]
  • [ 186517-01-1 ]
  • C16H10Br2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: tributyl(1-ethoxyvinyl)stannane; 2,6-dibromoanthracene With tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 85℃; for 16h; Inert atmosphere; Stage #2: With N-Bromosuccinimide; water In 1,4-dioxane at 20℃; for 1h; J3.J3a Step J3a. A mixture of 2,6-dibromoanthracene (0.300 g, 0.893 mmol), tributyl (1-ethoxy- vinyl)tin (0.31 mL, 0.893 mmol) and Pd(PPh3)4 (0.103 g, 89.3 μιηο) in 1,4-dioxane (9 mL) was degassed and heated at 85 °C under 2 for 16 hours before cooling. Water (3 mL) and NBS (0.167 g, 0.937 mmol) were added. The suspension was stirred at rt for 1 hour before partition (EtOAc-H20). The organics were washed with brine, dried (Na2S04), filtered and evaporated to afford a yellow solid, which was used directly for next step.
  • 44
  • [ 186517-01-1 ]
  • C30H32BrNO5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: tetrakis(triphenylphosphine) palladium(0) / 1,4-dioxane / 16 h / 85 °C / Inert atmosphere 1.2: 1 h / 20 °C 2.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 72 h / 20 °C
  • 45
  • [ 186517-01-1 ]
  • dimethyl 2,6-dibromo-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: toluene / Inert atmosphere; Reflux 1.2: Inert atmosphere; Reflux 2.1: sulfuric acid / Reflux
  • 46
  • [ 186517-01-1 ]
  • dimethyl 2,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: toluene / Inert atmosphere; Reflux 1.2: Inert atmosphere; Reflux 2.1: sulfuric acid / Reflux 3.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 80 °C / Inert atmosphere
  • 47
  • [ 186517-01-1 ]
  • C18H12Br2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere 2: bromine / 1,4-dioxane / 3 h / 20 °C
  • 48
  • [ 186517-01-1 ]
  • C29H33N3O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere 2.1: bromine / 1,4-dioxane / 3 h / 20 °C 3.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 4 h / 0 - 20 °C 3.2: 18 h / 130 °C
  • 49
  • [ 186517-01-1 ]
  • C34H27NO5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: toluene / 84 h / 150 °C / Sealed tube; Inert atmosphere 2: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / toluene; tetrahydrofuran; water / 23 h / 100 °C / Inert atmosphere
  • 50
  • [ 186517-01-1 ]
  • C28H24BrNO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: toluene / 84 h / 150 °C / Sealed tube; Inert atmosphere 2: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / toluene; tetrahydrofuran; water / 42 h / 100 °C / Inert atmosphere
  • 51
  • [ 186517-01-1 ]
  • C36H31NO5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: toluene / 84 h / 150 °C / Sealed tube; Inert atmosphere 2: CyJohnPhos; tetrakis(triphenylphosphine) palladium(0); potassium carbonate / toluene; tetrahydrofuran; water / 16 h / 100 °C / Inert atmosphere
  • 52
  • [ 186517-01-1 ]
  • C34H31NO5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: toluene / 84 h / 150 °C / Sealed tube; Inert atmosphere 2: CyJohnPhos; tetrakis(triphenylphosphine) palladium(0); potassium carbonate / toluene; tetrahydrofuran; water / 16 h / 100 °C / Inert atmosphere
  • 53
  • [ 110-89-4 ]
  • [ 186517-01-1 ]
  • 2,6-bis(piperidyl)anthracene [ No CAS ]
YieldReaction ConditionsOperation in experiment
54% With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) dichloride; sodium t-butanolate In 1,4-dioxane at 100℃; for 24h; Inert atmosphere;
  • 54
  • [ 186517-01-1 ]
  • [ 226065-37-8 ]
  • C36H38N4O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With tri-tert-butylphosphonium tetrafluoroborate; palladium diacetate; caesium carbonate In toluene at 20℃; Reflux; 2 Synthesis of reaction intermediate s7 Synthesis of reaction intermediate s7: A round bottom flask was filled with a compound s6 (2,6-dibromoanthracene) of about 444mg (1.32 mmol), a compound s2 (N-phenyl-hydrazinc carboxylic acid tert-butyl ester) of about 329 mg (1.55mmol), Cs2CO3 of about 602 mg (1.85 mmol), P(t-13u)3- H13F4 of about 5 mol %, Pd(OAc)2 of about 5 mol % and toluene anhydride of about 5 mE at room temperature. The reaction mixture was stirred for about 30 minutes and refluxed overnight. The reaction mixture obtained after thereaction was purified and isolated by colunm chromatography and the intermediate compound s7 of about 429 mg was obtained with a yield of about 55%. ‘HNMR (400 MHz, CDC13) ö 8.01 -6.78 (m, 14H), 6.40 (bs, 2H), 1.38 (s, 18H).
  • 55
  • [ 186517-01-1 ]
  • C26H16N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: caesium carbonate; tri-tert-butylphosphonium tetrafluoroborate; palladium diacetate / toluene / 20 °C / Reflux 2: hydrogenchloride / ethanol; water / 8 h / Reflux
  • 56
  • [ 25069-74-3 ]
  • [ 186517-01-1 ]
  • C54H40N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With palladium diacetate; sodium carbonate In N,N-dimethyl-formamide Inert atmosphere; Heating; 2.1.5. Synthesis of 2,6-DSAn 0.5 g of 2,6-dibromoanthracene (1.49 mmol), 0.95 g ofDPAS (3.5 mmol), 0.3 g of Na2CO3 and 0.04 g ofPd(OAc)2 were added to a round flask for nitrogen substitution.After adding 50 ml of DMF, the solution wasallowed to react for 2 hours at 130 C. The solutionwas extracted using chloroform and water, and moisturewas removed using MgSO4. The product was refined bycolumn chromatography to obtain 0.53 g of yellow solid(yield: 50%).1H-NMR (300 MHz, THF-d8, ): 8.35 (s, 2H), 7.96(m, 4H), 7.82 (d, 2H), 7.51 (d, 4H), 7.27 (m, 12H), 7.06(m, 16H).
50% With palladium diacetate; sodium carbonate In N,N-dimethyl-formamide at 130℃; for 2h; Glovebox; 2 compound A 0.5g (0.00149mol, 1eq) in a flask, compound B 0.95g (0.0035 mol, 1.2eq) and Na2CO3 were placed 0.3g (2eq). Then put the palladium (II) acetate, 0.04g (0.04eq) in the glove box, and then to put the semi 50ml DMF was reacted for 2 hours at 130 . Then it extracted using chloroform with demineralized water and dried with MgSO4. With acetone and then filtered liquid was purified by column chromatography (MC: hexane = 1: 2) to yield 0.53g of the compound represented by Formula 4a. The yield was 50%.
50% With palladium diacetate; sodium carbonate In N,N-dimethyl-formamide Glovebox; Heating; 2 Compound A 0.5g (0.00149mol, 1eq), compound B 0.95g (0.0035 mol, 1.2eq) and Na2CO3 0.3g (2eq) were added to a flask, palladium (II) acetate 0.04g (0.04eq) was added to the glove box, DMF 50ml was added and reacted at 130 degree C for 2 hours. The resulting mixture was extracted using chloroform and demineralized water and dried with MgSO4. The filtered liquid was washed with acetone and purified by column chromatography (MC: hexane = 1: 2) to yield 0.53 g of the compound represented by Formula 4a. The yield was 50%.
  • 57
  • [ 5720-07-0 ]
  • [ 186517-01-1 ]
  • 2,6-bis(4-methoxyphenyl)anthracene [ No CAS ]
YieldReaction ConditionsOperation in experiment
75.64% With tetrakis(triphenylphosphine) palladium(0); Aliquat 336; sodium carbonate In toluene at 95℃; for 24h; Sealed tube; 1 The preparation method of the organic semiconductor material 2,6-bis (4-methoxyphenyl) anthracene (BOPAnt) In a 250ml single-necked reaction flask,3.36 g of 2,6-dibromoanthracene (10 mmol), 150 ml of toluene,3.80 g of methoxyphenylboronate (25 mmol),25 ml of 2M sodium carbonate solution, 0.23 g of tetrakis (triphenylphosphine) palladium (0.2 mmol) and 2.7 g of trioctylmethylammonium chloride were charged, nitrogen was bubbled through the reaction solution for 25 minutes, the reactor was closed, the temperature was raised to 95 refluxed 24h, stop the reaction. Washed successively with methanol, dilute acid solution, acetone and chloroform, and filtered to obtain 2.95 g of a yellow product (yield 75.64%). The obtained product was BOPAnt.
With tetrakis(triphenylphosphine) palladium(0); cetyltrimethylammonim bromide; sodium carbonate In water; toluene at 85℃; for 36h; Inert atmosphere;
  • 58
  • [ 98546-51-1 ]
  • [ 186517-01-1 ]
  • C28H22S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); cetyltrimethylammonim bromide; sodium carbonate In water; toluene at 85℃; for 36h; Inert atmosphere;
  • 59
  • [ 63139-21-9 ]
  • [ 186517-01-1 ]
  • 2,6-bis[4-ethylphenyl]anthracene [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); cetyltrimethylammonim bromide; sodium carbonate In water; toluene at 85℃; for 36h; Inert atmosphere;
  • 60
  • [ 17997-47-6 ]
  • [ 186517-01-1 ]
  • 2,6-di(pyridin-2-yl)anthracene [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With tetrakis(triphenylphosphine) palladium(0) In toluene at 120℃; Inert atmosphere;
  • 61
  • [ 1692-15-5 ]
  • [ 186517-01-1 ]
  • [ 1287311-69-6 ]
YieldReaction ConditionsOperation in experiment
71% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 85℃; for 72h;
61% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In N,N-dimethyl-formamide at 110℃; for 24h; Inert atmosphere;
55% With potassium carbonate In 1,4-dioxane; water at 90℃; for 72h; Inert atmosphere; Glovebox;
38.9% With tetrakis(triphenylphosphine) palladium(0); water; potassium carbonate In ethanol; toluene at 90℃; Inert atmosphere;

  • 62
  • [ 1692-25-7 ]
  • [ 186517-01-1 ]
  • 2,6-di(pyridin-3-yl)anthracene [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With tetrakis(triphenylphosphine) palladium(0); water; potassium carbonate In ethanol; toluene at 90℃; Inert atmosphere;
  • 63
  • [ 186517-01-1 ]
  • C28H16Br4 [ No CAS ]
  • C28H16Br4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
35% In benzene at 80℃; for 24h; Inert atmosphere; UV-irradiation; Sealed tube;
  • 64
  • [ 79887-10-8 ]
  • [ 186517-01-1 ]
  • 2,6-bis(4-pentylphenylethynyl)anthracene [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; sodium iodide In toluene at 80℃; for 36h; Inert atmosphere; 2,6-Bis(4-pentylphenylethynyl)anthracene (1) To a mixture of 2,6-dibromoanthracene (305 mg,0.908 mmol),1 PdCl2(PPh3)2 (18.8 mg, 0.027 mmol), CuI (5.1 mg, 0.027 mmol), and NaI (136 mg, 0.907mmol) under Ar were added dry Et3N (18 mL) followed by a solution of 5 (469 mg, 2.72 mmol) in dry toluene (18 mL). The resulting mixture was stirred at 80 °C for 36 h under Ar and light shielding. After cooling to room temperature and evaporation of solvents, the residue was triturated with Et2O, filtered, and washed with Et2O, H2O, and MeOH. The filtered solid was purified by column chromatography on silica gel eluted with CHCl3, then by recycle preparative HPLC using a polystyrene gel column withCHCl3 as an eluent, and finally by reprecipitation with CHCl3-MeOH to give 1 (311 mg, 66% yield) as a pale yellow solid. Mp. 222 °C; 1H NMR (CD2Cl2) δ 8.40 (s, 2H), 8.22 (s, 2H), 8.00 (d, J = 8.8 Hz, 2H),7.56 (dd, J = 1.5 and 8.8 Hz, 2H), 7.51 (d, J = 8.3 Hz, 4H), 7.23 (d, J = 8.3 Hz, 4H), 2.65 (t, J = 7.8 Hz,4H), 1.64 (quint, J = 7.6 Hz, 4H), 1.37-1.33 (m, 8H), 0.91 (t, J = 7.1 Hz, 6H); 1H NMR (CDCl3) δ 8.36 (s,2H), 8.20 (s, 2H), 7.97 (d, J = 8.8 Hz, 2H), 7.55 (dd, J = 1.5 and 8.8 Hz, 2H), 7.52 (d, J = 8.3 Hz, 4H),7.21 (d, J = 8.3 Hz, 4H), 2.65 (t, J = 7.8 Hz, 4H), 1.65 (quint, J = 7.6 Hz, 4H), 1.38-1.32 (m, 8H), 0.91 (t,J = 6.8 Hz, 6H); 13C NMR (CDCl3) δ 143.83, 131.87, 131.83, 131.78, 131.36, 128.71, 128.47, 128.34,126.38, 121.03, 120.69, 91.20, 89.63, 36.11, 31.65, 31.02, 22.68, 14.11; HRMS (EI+) calcd for C40H38:518.2974, found: 518.2946. Anal. Calcd for C40H38: C, 92.62; H, 7.38. Found: C, 92.47; H, 7.57.
  • 65
  • [ 186517-01-1 ]
  • 1,1'-dimethyl-4,4'-(2,6-anthrylenedi-2,1-ethenediyl)dipyridinium diiodide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 1.2: 1 h / -78 °C 2.1: piperidine / ethanol / 24 h / 80 °C
  • 66
  • [ 186517-01-1 ]
  • [ 214360-73-3 ]
  • 2,6-bis(4-aminophenyl)anthracene [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; N,N-dimethyl-formamide at 110℃; for 24h; Inert atmosphere;
  • 67
  • 3,6-dioctyl-9H-carbazole [ No CAS ]
  • [ 186517-01-1 ]
  • 2,6-bis(3,6-dioctyl-9H-carbazol-9-yl)anthracene [ No CAS ]
YieldReaction ConditionsOperation in experiment
59% With tris-(dibenzylideneacetone)dipalladium(0); lithium hexamethyldisilazane; XPhos In tetrahydrofuran; 1,4-dioxane for 17h; Inert atmosphere; Schlenk technique; Heating;
  • 68
  • 4-methoxy-N-(4-methoxyphenyl)-N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]benzenamine [ No CAS ]
  • [ 186517-01-1 ]
  • 4,4'-(anthracene-2,6-diyl)bis(N,N-bis(4-methoxyphenyl)aniline) [ No CAS ]
YieldReaction ConditionsOperation in experiment
38.3% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In toluene at 120℃; for 48h; Inert atmosphere;
  • 69
  • [ 101-70-2 ]
  • [ 186517-01-1 ]
  • N<SUP>2</SUP>,N<SUP>2</SUP>,N<SUP>6</SUP>,N<SUP>6</SUP>-tetrakis(4-methoxyphenyl)anthracene-2,6-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
50.2% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate In toluene at 110℃; for 48h;
  • 70
  • [ 186517-01-1 ]
  • C20H18Br2N2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With diethylazodicarboxylate In toluene Reflux;
  • 71
  • C31H21BN2O2 [ No CAS ]
  • [ 186517-01-1 ]
  • C76H46N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene Inert atmosphere; Reflux; 28.2 (2) 9.28 g (0.02 mol) of intermediate C,2,6-dibromoanthracene 3.36 g (0.01 mol), potassium carbonate 4.15 g (0.03 mol), toluene 50 ml, ethanol 30 ml and water 30 ml were mixed, and tetrakis(triphenylphosphine)palladium 0.23 g was added under a nitrogen atmosphere ( The reaction was carried out, the temperature was raised to reflux, the plate was monitored until the reaction was completed, the reaction was completed, the reaction solution was spun dry, and 100 ml of dichloromethane was added thereto to dissolve completely and passed through a silica gel column. The filtrate was added with 100 ml of water, washed with water, and organic was separated. Phase, spin it dry and cook twice with ethanol, and filter to give 6.4 g of white solid compound G60.The yield was 65%.
  • 72
  • C33H23BN2O2 [ No CAS ]
  • [ 186517-01-1 ]
  • C80H50N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene Inert atmosphere; Reflux; 36.2 (2) 9.8 g (0.02 mol) of intermediate D, 2.66 g (0.01 mol) of 2,6-dibromoanthracene, 4.15 g (0.03 mol) of potassium carbonate, 50 ml of toluene, 30 ml of ethanol and 30 ml of water were mixed under nitrogen atmosphere. Then, 0.23 g (0.0002 mol) of tetrakis(triphenylphosphine)palladium was added to carry out the reaction, the temperature was raised to reflux, the plate was monitored until the reaction was completed, the reaction was terminated, the reaction solution was spun dry, and 100 ml of dichloromethane was added to dissolve it completely. After passing through a silica gel column, the filtrate was added with 100 ml of water, washed with water, and the organic phase was separated, dried, and boiled twice with ethanol, and filtered.6.5 g of white solid compound G88,The yield was 61%.
  • 73
  • C35H23BN2O2 [ No CAS ]
  • [ 186517-01-1 ]
  • C84H50N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene Inert atmosphere; Reflux; 50.2 (2) 10.28 g (0.02 mol) of intermediate N, 2,6-dibromoanthracene 3.36 g (0.01 mol), potassium carbonate 4.15 g (0.03 mol), toluene 50 ml, ethanol 30 ml and water 30 ml were mixed in a nitrogen atmosphere. Then, 0.23 g (0.0002 mol) of tetrakis(triphenylphosphine)palladium was added to carry out the reaction, the temperature was raised to reflux, the plate was monitored until the reaction was completed, the reaction was terminated, the reaction solution was spun dry, and 100 ml of dichloromethane was added to dissolve it completely. After passing through a silica gel column, the filtrate was added with 100 ml of water, washed with water, and the organic phase was separated, dried, and then boiled twice with ethanol and filtered to give 6.9 g of white solid compound G174.The yield was 62%.
  • 74
  • C37H23BN2O2S [ No CAS ]
  • [ 186517-01-1 ]
  • C88H50N4S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene Inert atmosphere; Reflux; 59.2 (2) 10.4 g (0.02 mol) of intermediate S, 2,6-dibromoanthracene 3.36 g (0.01 mol), potassium carbonate 4.15 g (0.03 mol), toluene 50 ml, ethanol 30 ml and water 30 ml were mixed in a nitrogen atmosphere. Then, 0.23 g (0.0002 mol) of tetrakis(triphenylphosphine)palladium was added to carry out the reaction, the temperature was raised to reflux, the plate was monitored until the reaction was completed, the reaction was terminated, the reaction solution was spun dry, and 100 ml of dichloromethane was added to dissolve it completely. After passing through a silica gel column, the filtrate was added with 100 ml of water, washed with water, and the organic phase was separated, dried and dried twice with ethanol and filtered to give 7.6 g of white solid compound G203.The yield was 62%.
  • 75
  • C33H21BN2O3 [ No CAS ]
  • [ 186517-01-1 ]
  • C80H46N4O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene Inert atmosphere; Reflux; 63.2 (2) 11.08 g (0.02 mol) of intermediate U, 2,6-dibromoanthracene 3.36 g (0.01 mol), potassium carbonate 4.15 g (0.03 mol), toluene 50 ml, ethanol 30 ml and water 30 ml were mixed in a nitrogen atmosphere. Then, 0.23 g (0.0002 mol) of tetrakis(triphenylphosphine)palladium was added to carry out the reaction, the temperature was raised to reflux, the plate was monitored until the reaction was completed, the reaction was terminated, the reaction solution was spun dry, and 100 ml of dichloromethane was added to dissolve it completely. After passing through a silica gel column, the filtrate was added with 100 ml of water, washed with water, and the organic phase was separated, dried and dried twice with ethanol and filtered to give 6.7 g of white solid compound G224.The yield was 62%
  • 76
  • C31H21BN2O2 [ No CAS ]
  • [ 186517-01-1 ]
  • C76H46N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene Inert atmosphere; Reflux; 49.2 (2) 9.28 g (0.02 mol) of intermediate N, 2,6-dibromoindole 3.36 g (0.01 mol),4.15 g (0.03 mol) of potassium carbonate, 50 ml of toluene, 30 ml of ethanol and 30 ml of water were mixed.The reaction was carried out by adding 0.23 g (0.0002 mol) of tetrakis(triphenylphosphine)palladium under a nitrogen atmosphere.The temperature was raised to reflux, the spot plate was monitored until the reaction was completed, the reaction was terminated, the reaction solution was spun dry, 100 ml of dichloromethane was added, and the solution was completely dissolved and passed through a silica gel column. The filtrate was added with 100 ml of water, washed with water, and the organic phase was separated and dried. It was further boiled twice with ethanol and filtered to obtain 6.4 g of a white solid compound G173 in a yield of 63%.
  • 77
  • [ 867044-33-5 ]
  • [ 186517-01-1 ]
  • C52H34N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene;Inert atmosphere; Reflux; 6.28 g (0.02 mol) of intermediate G25-1, 2.66 g (0.01 mol) of 2,6-dibromofluorene,4.15 g (0.03 mol) of potassium carbonate, 50 ml of toluene, 30 ml of ethanol and 30 ml of water were mixed.The reaction was carried out by adding 0.23 g (0.0002 mol) of tetrakis(triphenylphosphine)palladium under a nitrogen atmosphere.The temperature was raised to reflux, the spot plate was monitored until the reaction was completed, the reaction was terminated, the reaction solution was spun dry, 100 ml of dichloromethane was added, and the solution was completely dissolved and passed through a silica gel column. The filtrate was added with 100 ml of water, washed with water, and the organic phase was separated and dried. It was boiled twice with ethanol and filtered to obtain 4.3 g of a white solid compound G25-2 in a yield of 60%.
  • 78
  • [ 867044-33-5 ]
  • [ 186517-01-1 ]
  • C52H32Br2N4 [ No CAS ]
  • 79
  • [ 952514-79-3 ]
  • [ 186517-01-1 ]
  • C52H34N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene;Inert atmosphere; Reflux; 6.28 g (0.02 mol) of intermediate G26-1, 2.66 g (0.01 mol) of 2,6-dibromoindole, 4.15 g (0.03 mol) of potassium carbonate, 50 ml of toluene, 30 ml of ethanol and 30 ml of water were mixed under a nitrogen atmosphere. The reaction was carried out by adding 0.23 g (0.0002 mol) of tetrakis(triphenylphosphine)palladium, and the temperature was raised to reflux. The reaction was completed until the reaction was completed. The reaction was terminated, and the reaction solution was spun dry, and 100 ml of dichloromethane was added to dissolve it completely. The silica gel column and the filtrate were added with 100 ml of water, washed with water, and the organic phase was separated, dried, and then, then, and dried twice with ethanol and filtered to give 4.5 g of white solid compound G26-2, yield 61%.
  • 80
  • [ 952514-79-3 ]
  • [ 186517-01-1 ]
  • C52H32Br2N4 [ No CAS ]
  • 81
  • C31H21BN2O2 [ No CAS ]
  • [ 186517-01-1 ]
  • C76H46N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene Inert atmosphere; Reflux; 19.2 (2) 9.28 g (0.02 mol) of intermediate B, 2.66 g (0.01 mol) of 2,6-dibromoindole, 4.15 g (0.03 mol) of potassium carbonate, 50 ml of toluene, 30 ml of ethanol and 30 ml of water were mixed under nitrogen atmosphere. Then, 0.23 g (0.0002 mol) of tetrakis(triphenylphosphine)palladium was added to carry out the reaction, the temperature was raised to reflux, the plate was monitored until the reaction was completed, the reaction was terminated, the reaction solution was spun dry, and 100 ml of dichloromethane was added to dissolve it completely. After passing through a silica gel column, the filtrate was added with 100 ml of water, washed with water, and the organic phase was separated, dried, and boiled twice with ethanol, and filtered.6.6 g of white solid compound G34,The yield was 65%.
  • 82
  • (4-(1-phenyl-1H-phenanthro[9,10-d]imidazol-2-yl)phenyl)boronic acid [ No CAS ]
  • [ 186517-01-1 ]
  • C68H42N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene Inert atmosphere; Reflux; 6.2 (2) 8.28 g (0.02 mol) of intermediate A,2,6-dibromofluorene 3.36g (0.01mol),4.15 g (0.03 mol) of potassium carbonate, 50 ml of toluene, 30 ml of ethanol and 30 ml of water were mixed, and 0.23 g (0.0002 mol) of tetrakis(triphenylphosphine)palladium was added under a nitrogen atmosphere to carry out a reaction, and the mixture was heated to reflux. The reaction was completed, the reaction was completed, the reaction solution was spun dry, 100 ml of dichloromethane was added, and the solution was completely dissolved and passed through a silica gel column. The filtrate was added to 100 ml of water, and the organic phase was separated by washing with water, dried and then boiled twice with ethanol and filtered. 6.5g of light yellow solid compound G8,The yield was 70%.
  • 83
  • (4-(1-phenyl-1H-phenanthro[9,10-d]imidazol-2-yl)phenyl)boronic acid [ No CAS ]
  • [ 186517-01-1 ]
  • C41H25BrN2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene Inert atmosphere; Reflux; 11.1 4.14 g (0.01 mol) A, 3.36 g (0.01 mol)2,6-dibromoanthracene, 4.15 g (0.03 mol) of potassium carbonate, 50 ml of toluene, 30 ml of ethanol and 30 ml of water were mixed, and 0.23 g (0.0002 mol) of tetrakis(triphenylphosphine)palladium was added under a nitrogen atmosphere, and the mixture was heated to reflux to carry out a reaction. The reaction was completed, the reaction was completed, the reaction solution was dried, and 100 ml of dichloromethane was added. The solution was completely passed through a silica gel column, and the filtrate was added to 100 ml of water, washed with water, and the organic phase was separated, dried, and then hot-digested twice with ethanol, and filtered to obtain 4.5 g of white solid intermediate G16-1, yield 73%.
  • 84
  • C18H24O [ No CAS ]
  • [ 186517-01-1 ]
  • C50H54O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% With palladium diacetate; caesium carbonate; johnphos In tetrahydrofuran at 130℃; for 24h; Inert atmosphere; Sealed tube;
Same Skeleton Products
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