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Product Details of 4-tert-Butylphenylboronic acid

CAS No. :123324-71-0
Formula : C10H15BO2
M.W : 178.04
SMILES Code : CC(C1=CC=C(B(O)O)C=C1)(C)C
MDL No. :MFCD01009697
InChI Key :MNJYZNVROSZZQC-UHFFFAOYSA-N
Pubchem ID :2734320

Safety of 4-tert-Butylphenylboronic acid

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of 4-tert-Butylphenylboronic acid

* 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 [ 123324-71-0 ]

[ 123324-71-0 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 619-44-3 ]
  • [ 123324-71-0 ]
  • [ 1625-91-8 ]
  • methyl 4'-(tert-butyl)-[1,1'-biphenyl]-4-carboxylate [ No CAS ]
  • 2
  • [ 42872-74-2 ]
  • [ 123324-71-0 ]
  • 4'-<i>tert</i>-butyl-6-methyl-biphenyl-3-carbonitrile [ No CAS ]
  • 3
  • [ 123324-71-0 ]
  • [ 1625-91-8 ]
YieldReaction ConditionsOperation in experiment
95% With copper(II) choride dihydrate; sodium carbonate; In methanol; at 25℃; for 0.25h;Green chemistry;Catalytic behavior; General procedure: Arylboronic acid (0.3 mmol), CuCl2·2H2O (2.5 mg, 5 molpercent), Na2CO3 (10 molpercent),methanol (1 mL) were added to a vial. The reaction mixture was stirred at 25 °C inthe air for 5-15 min and was monitored by TLC. Then the reaction was quenched withtwo drops of H2O, diluted with 2 mL of ethyl acetate, and filtered over a pad ofMgSO4 and silica. The pad was rinsed with additional ethyl acetate, and the solutionwas concentrated in vacuum. The crude material was loaded onto a silica gel columnand purified by flash chromatography.
91% With oxygen; potassium carbonate; In water; at 25℃; for 2h;Green chemistry; General procedure: A solution of nano CuO (0.010 mmol) and substituted phenylboronic acid (1 mmol) in H2O (2 mL) was stirred at 25 °C for 2 h under aerobic condition. After the reaction was over, the reaction mixture was extracted with ethyl acetate and washed with doubledistilled water in a separating funnel. The organic layer was separated and collected in a conical flask. After evaporation of the solvent in a rotary evaporator, reaction mixture was subjected to column chromatography on silica gel column (ethyl acetate/hexane, 1:10) to afford the respective product.
90% With Cu2(ophen)2; In N,N-dimethyl-formamide; at 20℃; for 20h; General procedure: 4.3. Catalytic tests: general procedure I for the Cu2(ophen)2catalyzed homocoupling for Table 2 A solution of the corresponding arylboronic acids (1.0 mmol),Cu2(ophen)2 (1.3 mg, 0.5 mol percent), DMF (1.0 mL) in 5 mL round-bottomed ask was stirred under air and the reaction was moni-tored by TLC. After the substrate was consumed, the reaction con-versions were determined bygas chromatography (GC) analysis (FIDfrom AGILENT 7820) using a cross-linked (95percent)-dimethyl-(5percent)-diphenylpolysil-oxane column (HP-5, 30 m0.32 mm0.25 mm),helium, injector temperature 250 C, detector temperature 300 C,and oven temperature program 45 C (3 min)e20C/mine280 C(2 min). The resulting mixture was poured into brine (10 mL), andextracted with diethyl ether (310 mL). The organic layer waswashed with brine, dried over Mg2SO4, the residue was chromato-graphed via a short column of silica gel (petroleum ether: diethylether15:1) and evaporated under reduced pressure. The productswas determined by 1H NMR spectroscopy. All 1H NMR spectra weremeasured in CDCl3 with TMS as the internal standard.
75% With [Cu(trans-cyclohexane-1,2-diamine)2(H2O)2][OTf]2; In methanol; at 20℃; for 3h; General procedure: In a 25-mL round-bottomed flask, a solution of copper(II)complex (2 mol percent) and substituted phenylboronic acid (1.5 mmol)in methanol (5 mL) was stirred at room temperature for 3e4 h. Theprogress of the reaction was monitored by TLC. After completion ofthe reaction, the solvent was removed and the product was washedwith water and extracted with ethyl acetate (3 10 mL). Thecombined organic layers were dried over Na2SO4 and the solventremoved under reduced pressure to give crude product which waspurified by column chromatography by using petroleum ether/ethyl acetate (4:1) as an eluent.
72% With sodium tetrachloroaurate(III) dihyrate; potassium carbonate; In ethanol; at 50℃; for 24h; Representative experimental procedure: A mixture of AuCl (11.6 mg, 0.050 mmol), phenylboronic acid (1a, 121.9 mg, 1.00 mmol), K2CO3 (152.0 mg, 1.10 mmol) in EtOH (8.0 mL) was heated at 50 °C under open air for 24 h. The reaction mixture was filtered through a plug of Florisil.(R). washing with hexane-AcOEt (3:1). The filtrate was concentrated under reduced pressure, and the resulting residue was subjected to preparative thin-layer chromatography (hexane:AcOEt = 20:1) to afford biphenyl (2a, 58.6 mg, 76percent).
With oxygen; caesium carbonate; In N,N-dimethyl-formamide; at 20℃; for 1h; In a 25 mL beaker1 g of 4-tert-butylbenzeneboronic acid, 0.2 g of Cs2C03, 3 mL of DMF and (hi g catalyst (complex 1)The reaction was complete, 10 mL of CH2CI2 was extracted and washed with 20 mL of distilled water. The organic phase was dried with sewage MgS04, filtered and the solution was removed and the crude product was obtained. The reaction mixture was stirred at room temperature for 1 hour. The petroleum ether eluted the column to give 4,4-di-tert-butylbiphenyl.
With Cu(1+)*BF4(1-)*C10H8N6*0.5H2O; caesium carbonate; In N,N-dimethyl-formamide; At 25 mL Weigh 1 g in the beaker 4-tert-butylbenzeneboronic acid, 0.2 g Cs2C03, 3 mL DMF and 0.1 g catalyst (Complex 1), The mixture was stirred at room temperature for 1 hour, TLC monitoring (RhoEpsilon: EpsilonAlpha = 1: 1) The reaction was complete, 10 mL of CH2CI2 after extraction of the product And then washed with 20 mL of distilled water, Organic phase with sewage MgS04 dry, Filtration, desolvation, The resulting crude product was eluted with petroleum ether Column, get 4,4-di-tert-butylbiphenyl
With {Cu(1-(4-(4-(1H-1,2.4-triazol-1-yl)phenoxy)phenyl)-1H-1,2.4-triazole)2(NO3)2}; oxygen; caesium carbonate; at 20℃; for 1h; Weigh 1 g of 4-tert-butylphenylboronic acid in a 25 mL beaker, 0.2 g Cs2CO3, 3 mL DMF and 0.1 g catalyst (complex1), Stir at room temperature for 1 hour, TLC monitoring (PE:EA = 1:1) Complete reaction, 10 mL CH2Cl2The product is extracted and washed with 20 mL of distilled water. The organic phase is treated with effluent MgSO?4Drying, filtration, desolvation, and the resulting crude product was eluted through a column with petroleum ether to give 4,4'-di-tert-butylbiphenyl.

  • 4
  • [ 123324-71-0 ]
  • [ 171408-84-7 ]
  • 2,7-bis(4-tert-butylphenyl)-9,9'-spirobifluorene [ No CAS ]
  • 5
  • [ 121-43-7 ]
  • [ 3972-65-4 ]
  • [ 30913-86-1 ]
  • [ 123324-71-0 ]
  • 4-(4'-tert-Butyl-biphenyl-4-yl)-4-oxo-butyric acid methyl ester [ No CAS ]
  • 4-(4'-tert-butyl-biphenyl-4-yl)-4-hydroxyimino-butyric acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; n-butyllithium;sodium carbonate; tetrakis(triphenylphosphine)palladium (0); In tetrahydrofuran; diethyl ether; toluene; Step (a) Preparation of 4-(4'-tert-Butyl-biphenyl-4-yl)-4-oxo-butyric acid methyl ester To a stirred solution of 4-tert-butyl-bromobenzene (21.3 g, 0.0999 mol) in THF (30 mL) at -78 C. under nitrogen was added dropwise a 2.1 M solution of n-butyl lithium in hexanes (45 mL, 0.095 mol), and the mixture was stirred for 1.5 hours. To the mixture was added dropwise neat trimethylborate (10.2 mL, 0.090 mol), and the mixture was allowed to slowly warm to room temperature. The mixture was stirred overnight, then quenched by dropwise addition of 1.0 M aqueous hydrochloric acid. Brine was added, and the organic layer was dried (Na2SO4) and rotary evaporated. The residue was crystallized from n-heptane to give 4.65 g of crude 4-tert-butyl-phenyl-boronic acid as white needles. This material was used directly in the next reaction without further characterization. Thus, in a manner similar to Example 12, Step (b), 4-tert-butyl-phenyl-boronic acid (0.4287 g, 0.00241 mol) was allowed to react with 4-(4-bromo-phenyl)-4-oxo-butyric acid, methyl ester (0.5443 g, 0.00200 mol) in the presence of tetrakis(triphenylphosphine)palladium(0) (0.0472 g, 0.0000408 mol) and 2.0 M aqueous sodium carbonate (2.4 mL, 0.0048 mol) in toluene (5 mL) to give, after chromatography on silica gel (270 g, 230-400 mesh), eluding with toluene then chloroform, 0.50 g. The material was dissolved in diethyl ether, washed with 0.10 M aqueous sodium hydroxide, water and brine. The organics were dried (K2CO3), and rotary evaporated to give 0.45 g of 4-(4'-tert-butyl-biphenyl-4-yl)-4-oxo-butyric acid, methyl ester as a white solid; mp 58-62 C.
  • 6
  • [ 28479-22-3 ]
  • [ 123324-71-0 ]
  • N-(3-chloro-4-methylphenyl)-4-(1,1-dimethylethyl)-benzamide [ No CAS ]
  • [ 1625-91-8 ]
  • 7
  • [ 103-71-9 ]
  • [ 123324-71-0 ]
  • [ 1625-91-8 ]
  • [ 65861-72-5 ]
  • 8
  • [ 123324-71-0 ]
  • [ 142404-82-8 ]
  • [ 1171975-45-3 ]
YieldReaction ConditionsOperation in experiment
85% With caesium carbonate;tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine; In 1,4-dioxane; at 20 - 90℃; (3); 4-t-Butylphenyl boronic acid (7.21 mmol, 1.28 g),Tris(dibenzylideneacetone)dipalladium(0) (0.20 mmol, 180 mg), tricyclohexylphosphine (1.31 mmol, 368 mg) and cesium carbonate (19.66 mmol, 6.41 g) were successively added to a dioxane solution (30 ml) of 2-(acetylamino)-amino-5- bromo-4-picoline (6.55 mmol, 1.5 g) at room temperature, and the temperature was elevated to 90C, followed by stirring for 9.5 hours. Water (30 ml) was added to the resulting reaction mixture on ice to stop the reaction, and an aqueous layer was extracted with ethyl acetate. An organic layer was washed with saturated saline, dried over anhydrous sodium sulfate, and filtered, followed by distilling away a solvent under reduced pressure. The resulting crude product was purified with column chromatography to obtain 1.58 g of 2-(acetylamino)-amino-5-(4-t-butylphenyl)-4- picoline (yield 85%). 1H NMR δ ppm (300 MHz, CDCl3) data of this compound are 8.10 (s, IH), 8.09 (s, IH), 7.98 (brs, IH), 7.45 (d, 2H, J=8.4Hz), 7.23 (d, 2H, J=8.7 Hz), <n="17"/>2.33 (s, 3H), 2.22 (s, 3H), 1.36 (s, 9H).
  • 9
  • [ 3141-24-0 ]
  • [ 123324-71-0 ]
  • [ 1208903-02-9 ]
  • 10
  • [ 1003-91-4 ]
  • [ 123324-71-0 ]
  • [ 1246624-44-1 ]
  • 11
  • [ 108-91-8 ]
  • [ 123324-71-0 ]
  • [ 1625-91-8 ]
  • N-(4-tert-butylphenyl)-N-cyclohexylamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
25% With oxygen; triethylamine;basolite C300; In dichloromethane; at 20℃; for 5h;Product distribution / selectivity; EXAMPLES[0008] MOF-199 (Basolite C300, Aldrich) , cyclohexylamine, triethylamine, phenylbornic acid, 4-nitrophenylboronic acid, 4-cyanophenylbornic acid, 4-chlorophenylboronic acid, 4-ter- burlyphenylboronic acid, 4- (dimehtylamino) -phenylboronic acid, naphthalene-1-bonronic acid and 1, 3, 5-trimethyoxybenzene were purchased form Aldrich Chemical Co.[0009] General homo-coupling reaction procedure:[0010] Cu3(BTC)2 (Basolite C300, provided by BASF,www.mof.basf.com, Aldrich catalogue number: 688614),cyclohexylamine, triethylamine, phenylboronic acid, 4- nitrophenylboronic acid, 4-cyanophenylboronic acid, 4- chlorophenylboronic acid, 4-tert-butylphenylboronic acid, 4-(dimethylamino) -phenylboronic acid, naphthyl-1-boronic acid and 1, 3, 5-trimethoxybenzene were purchased from AldrichChemical Co. Dichloromethane was purchased from FisherScientific International Inc. All starting materials were used without further purification. All experimental operations, unless otherwise noted, were performed in air. A mixture of arylboronic acid, (3.01 mmol) , cyclohexylamine (0.248 g, 286 muL, 2.51 mmol) and triethylamine (0.253 g, 348 muL, 2.49 mmol) were premixed and dissolved in 20 mL dichloromethane in a 50 mL round-bottom flask. MOF (0.100 g, 0.165 mmol, 0.495 mmol Cu(II)) or cupric acetate monohydrate (Cu (OAc) 2'H2O, 0.100 g, 0.501 mmol) was then added to the solution. The mixture was stirred at room temperature for 5 h, followed by filtration and washing with fresh dichloromethane. The excessdichloromethane in the filtrate was subsequently removed by rotovap . 1, 3, 5-trimethoxybenzene (0.168 g, 1.00 mmol) was added to the filtrate as internal standard for 1H NMR. Chemical shifts of all products in 1H NMR agree well with literature data .[0011] Biphenyl: 47percent yield of biphenyl (based onphenylboronic acid) was afforded when MOF was used; no biphenyl product was formed in the case of cupric acetate monohydrate. GC-MS, m/z+ 154.1; 4, 4' -dinitrobiphenyl : 87percent and 18percent yields of 4, 4' -dinitrobiphenyl (based on 4- nitrophenylboronic acid) were afforded when MOF and cupric acetate monohydrate were used, respectively. GC-MS, m/z+ 244.2; Biphenyl-4, 4' -dicarbonitrile : 92percent and 19percent yields of biphenyl-4, 4' -dicarbonitrile (based on 4-cyanophenylboronic acid) were afforded in the presence of MOF and cupric acetate monohydrate, respectively. 1.34 mmol (yield: 90percent) and 1.35 mmol (yield: 92percent) biphenyl-4, 4' -dicarbonitrile were observed in the second and third cycles, respectively. GC-MS, m/z+ 204.1; 4,4'-dichlorobiphenyl: 81percent and 8percent yields of 4,4'- dichlorobiphenyl (based on 4-chlorophenylboronic acid) were afforded in the presence of MOF and cupric acetatemonohydrate, respectively. GC-MS, m/z+ 223.1; 4, 4' -di-tert- butylbiphenyl : 25percent yield of 4, 4' -di-tert-butylbiphenyl (based on 4-tert-butylphenylboronic acid) was afforded when MOF was used, but none was formed in the case of cupric acetate monohydrate. GC-MS, m/z+ 266.1; N, N, N' ,N' -tetramethyldiphenyl- 4,4'-diamine: 43percent and 5percent yields of N, N, N', N'- tetramethyldiphenyl-4, 4' -diamine (based on 4- (dimethylamino) - phenylboronic acid) for MOF and cupric acetate monohydrate, respectively. GC-MS, m/z+ 240.1; 1, 1' -binaphthyl : 90percent and 6percent yields of 1, 1' -binaphthyl (based on naphthalyl-1-boronic acid) were afforded for MOF and cupric acetate monohydrate, respectively. GC-MS, m/z+ 254.2.[0012] Powder X-ray diffraction (PXRD) data were collected using a Bruker D8-Discover Psi-2Psi diffractometer in reflectance Bragg-Brentano geometry. Cu Ka radiation (lambda = 1.5406 A; 1,600 W, 40 kV, 40 mA) was focused using a planer Gobel Mirror riding the Ka line. A 0.6 mm divergence slit was used for all measurements. Diffracted radiation was detected using a Vantec line detector (Bruker AXS) (6° 2Psi sampling width) equipped with a Ni monochrometer . All samples were ground to ensure mono dispersity in the bulk, and then mounted onto a glass slide fixed on a sample holder by dropping powders and then leveling the sample surface with a wide-blade spatula. The best counting statistics were achieved by using a 0.02° 2Psi step scan from 1 - 50° with an exposure time of 0.4 s per step. The diffraction patterns collected for Cu3(BTC)2 both before and after homo-couplings are shown in Figures 4-10. Powder patterns of Cu3 (BTC)2 after three cycles alsoillustrated in Figure 11.[0013] FT-IR spectra of benzyltricarboxylic acid (BTC) and Cu3(BTC)2 (fresh and after coupling reaction) were obtained as KBr pellets using Nicolet 400 Impact spectrometer. FT-IR of recovered liquid after coupling reaction was performed on two clear KBr crystal plates. As shown in Figure 12 and 13, the C=O stretch of carboxylates in Cu3(BTC)2 absorbs at 1653 cm-1, whereas the C=O stretch of free carboxylic acid in BTC absorbs at 1734 cm'1, which is a strong characteristic peak for presence of any non-coordinated carboxylic groups. Recov...
  • 12
  • [ 214045-86-0 ]
  • [ 123324-71-0 ]
  • [ 1372215-45-6 ]
  • 14
  • [ 3621-82-7 ]
  • [ 123324-71-0 ]
  • [ 1421278-29-6 ]
YieldReaction ConditionsOperation in experiment
72% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 80℃; for 6h;Inert atmosphere; General procedure: A 1,4-dioxane solution (3 mL) of 1, arylboronic acid (1.2 equiv), aqueous K2CO3 (2.0 M, 1.0 mL) and Pd(PPh3)4 (3 mol percent) was heated at 80 °C for 6 h under argon atmosphere. After cooling to 20 °C, H2O was added and the reaction mixture was extracted with CH2Cl2 (3×25 mL). The organic layers were dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (silica gel, heptane/EtOAc).#10;
  • 15
  • [ 58421-80-0 ]
  • [ 123324-71-0 ]
  • [ 1446863-22-4 ]
  • C19H18Br2N2 [ No CAS ]
  • 16
  • [ 58421-80-0 ]
  • [ 123324-71-0 ]
  • [ 1446863-20-2 ]
YieldReaction ConditionsOperation in experiment
67% With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In 1,2-dimethoxyethane; at 85℃; for 1h; A 50-mL round bottom flask equipped with a magnetic stirrer,a condenser and a nitrogen in/outlet adapter was charged with<strong>[58421-80-0]4-chloro-8-methylquinazoline</strong> (200 mg, 1.12 mmol), 4-tert-butylphenylboronic acid (300 mg, 1.68 mmol), DME (12 mL), Na2CO3(5.0 ml)(2M). The resulting solution wasdegassed for 15 min, then Pd(PPh3)4 (130 mg, 0.112 mmol) was added. The reaction mixture was warmed to 85oCand stirred for 1 h. After cooled to roomtemperature, the reaction mixture was diluted with EtOAc and washed with saturatedNaHCO3, brine, dried over Na2SO4. The organiclayer was concentrated in rotavapor and purified on silica gel. Elution with EtOAc/hexanes solvent systemafforded the title compound (210 mg, 67% yield). 1H NMR (CDCl3, 400 MHz) delta 9.39 (s, 1H), 8.02 (d, J= 8.4 Hz, 1H), 7.72 (m, 3H), 7.57 (d, J= 8.0 Hz, 2H), 7.54 (m, 1H), 2.83 (s, 3H), 1.39 (s, 9H).
67% c. Preparation of Compound 12c A 50-mL round bottom flask equipped with a magnetic stirrer, a condenser and a nitrogen in/outlet adapter was charged with <strong>[58421-80-0]4-chloro-8-methylquinazoline</strong> 12b (200 mg, 1.12 mmol), 4-/ert-butylphenylboronic acid (300 mg, 1.68 mmol), DME (12 mL), Na2C03 (5.0 ml)(2M). The resulting solution was degassed for 15 min, then Pd(PPh3)4 (130 mg, 0.112 mmol) was added. The reaction mixture was warmed to 85C and stirred for 1 h. After cooled to room temperature, the reaction mixture was diluted with EtOAc and washed with saturated NaHC03, brine, dried over Na2S04. The organic layer was concentrated under reduced pressure and purified on silica gel. Elution with EtOAc/hexanes solvent system afforded the title compound (210 mg, 67% yield). 1H NMR (CDC13, 400 MHz) delta 9.39 (s, 1H), 8.02 (d, J- 8.4 Hz, 1H), 7.72 (m, 3H), 7.57 (d, J= 8.0 Hz, 2H), 7.54 (m, 1H), 2.83 (s, 3H), 1.39 (s, 9H).
67% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; at 85℃; for 1h;Inert atmosphere; A 50-mE round bottom flask equipped with a magnetic stirrer, a condenser and a nitrogen inoutlet adapter was charged with <strong>[58421-80-0]4-chloro-8-methylquinazoline</strong> 12b (200 mg, 1.12 mmol), 4-tert-butylphenylboronic acid (300 mg, 1.68 mmol), DME (12 mE), Na2CO3 (5.0 ml)(2M). The resulting solution was degassed for 15 mm, then Pd(PPh3)4 (130 mg, 0.112 mmol) was added. The reaction mixture was warmed to 85 C. and stirred for 1 h. Afier cooled to room temperature, the reaction mixture was diluted with EtOAc and washed with saturated NaHCO3, brine, dried over Na2SO4. The organic layer was concentrated under reduced pressure and purified on silica gel. Elution with EtOAc/hexanes solvent system afforded the title compound (210 mg, 67% yield). 1H NMR (CDCl3, 400 MHz) oe 9.39 (s, 1H), 8.02 (d, J=8.4 Hz, 1H), 7.72 (m, 3H), 7.57 (d, J=8.0 Hz, 2H), 7.54 (m, 1H), 2.83 (s, 3H), 1.39 (s, 9H).
  • 17
  • [ 74204-00-5 ]
  • [ 123324-71-0 ]
  • C17H20O [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 100℃; for 3.0h;Inert atmosphere; A 25-mL round bottom flask equipped with a magnetic stirrer, a condenser and a nitrogen in/outlet adapter was charged with <strong>[74204-00-5]3-bromo-5-methylphenol</strong> (300 mg, 1.6 mmol), 4- tert-butylphenylboronic acid (428 mg, 2.1 mmol), water/dioxane (1 mL/3 ml), K2C03 (441 mg, 3.2 mmol). The resulting solution was degassed for 5 minutes, then Pd(PPh3)4 (60 mg) was added. The reaction mixture was warmed to 100 °C and stirred for 3 hours. After being allowed to cool to room temperature, the reaction mixture was diluted with EtOAc (100 mL) and washed with saturated NaHCO3, brine, dried over Na2SO4. The organic layer was concentrated uiider reduced pressure and purified on silica gel. Elution with EtOAc/hexanes solvent system
  • 18
  • [ 221044-05-9 ]
  • [ 123324-71-0 ]
  • 2-(4-(tert-butyl)phenyl)-1-(pyrimidin-2-yl)-1H-indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver trifluoroacetate; In methanol; at 60℃;Schlenk technique; Inert atmosphere; General procedure: A mixture of N-pyrimidyl indoles 1 (0.20 mmol, 1.0 equiv.), arylboronicacids 2 (0.40 mmol, 2.0 equiv.),AgOOCF3 (0.80 mmol, 4.0 equiv.), and [RhCp*Cl2]2(0.002 mmol, 0.01 equiv.) were combined in MeOH (1.0 mL) in a dried Schlenk tubeunder a argon atmosphere. The resulting mixture was stirred at 60 C andmonitored by TLC. Uponcompletion or no further improvement of reaction, the reaction mixture wascooled to room temperature and added with Et3N (1 mL). Then themixture was filtered through a pad of silica gel eluting with 25 mL of CH2Cl2.The solvent was removed under reduced pressure and the residue was purified byflash chromatography on silica gel to afford the desired products.
  • 19
  • [ 1813-33-8 ]
  • [ 123324-71-0 ]
  • [ 935520-44-8 ]
YieldReaction ConditionsOperation in experiment
With 1,1'-bis-(diphenylphosphino)ferrocene; tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; toluene; for 12h;Reflux; General procedure: A mixture of 2-chloro-4-(trifluoromethyl)-benzonitrile (1.00 mmol), appropriate boronic acid (1.20 mmol)were dissolved in toluene/dioxane:2 N Na2CO3 (2:1:1) solution(6 ml). Tetrakis(triphenyl-phosphine)palladium(0) (0.10 mmol)and 1,10-Ferrocenediyl-bis(diphenylphosphine) (0.20 mmol) wasadded to the mixture and it was refluxed for 12 h. After cooleddown to ambient temperature, the reaction was filtered over celiteand extracted with EtOAc twice. The combined organic extractswere dried over MgSO4, filtered, and concentrated in vacuo. Theresidue was purified by flash column chromatography on silicagel using EtOAc/hexanes (1:10) eluant condition. (R-B(OH)2 =1-pentenyl boronic acid for 53, 1-cyclohexenylboronicacid for 54).
  • 20
  • [ 123324-71-0 ]
  • [ 98-54-4 ]
  • [ 1625-91-8 ]
YieldReaction ConditionsOperation in experiment
7%Chromat.; 90%Chromat. With Cu2(ophen)2; water; In ethanol; at 20℃;Green chemistry; General procedure: 4.4. General procedure II for Table 3 A solution of arylboronic acids (1.0 mmol), Cu2(ophen)2 (1.3 mg,0.5 mol percent) in H2O-EtOH (1.8 mL, VH2O:VEtOHn:1) was stirred atroom temperature. After the substrate was consumed, the reactionconversions were determined by GC analysis.
  • 22
  • C20H27BN2 [ No CAS ]
  • [ 68176-57-8 ]
  • [ 123324-71-0 ]
  • 23
  • [ 3972-65-4 ]
  • [ 123324-71-0 ]
  • [ 1625-91-8 ]
YieldReaction ConditionsOperation in experiment
96% With C21H19N2(1+)*Br(1-); palladium diacetate; potassium carbonate; In toluene; at 70℃; for 3h; General procedure: A reaction tube was charged with Pd(OAc)2 (1.34 mg, 0.006 mmol), imidazolium salt (0.0072 mmol), K2CO3 (62 mg, 0.45 mmol), and ArB(OH)2 (0.45 mmol). To the reaction tube were added toluene (2.0 mL) and aryl bromide (0.3 mmol). The mixture was stirred at 70 °C in the presence of air for 3 hours. The mixture was cooled to room temperature and directly purified through silica gel column chromatography to give the product.
  • 24
  • [ 88-12-0 ]
  • [ 383-62-0 ]
  • [ 123324-71-0 ]
  • ethyl 4-(4-(tert-butyl)phenyl)-2,2-difluoro-4-(2-oxopyrrolidin-1-yl)butanoate [ No CAS ]
  • 25
  • C13H12AuF2N [ No CAS ]
  • [ 123324-71-0 ]
  • [ 98-51-1 ]
  • [ 1625-91-8 ]
  • 26
  • [ 69884-16-8 ]
  • [ 123324-71-0 ]
  • [ 1625-91-8 ]
  • N-(2-tert-butylphenyl)-N-(4-tert-butylphenyl)amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
34 mg; 81% Into an argon filled two-neck flask fitted with reflux condenser and pressure-equalizing dropping funnel and containing CuCl (79 mg, 0.80 mmol), a solution of o-tert-butylnitrosobenzene 3a (130 mg, 0.80 mmol) in dry deaerated DMF (20 ml) was added. The mixture was stirred at 60°C (water bath) for 30 min. Then the solution of p-tert-butylphenylboronic 4b (155 mg, 0.87 mmol) acid in dry deaerated DMF (7 ml) was added and the mixture was stirred at 60°C for 16 h. The colour of the solution changed from light green to black via light yellow, green and greenish blue. Afterwards the mixture was diluted with water (100 ml) and saturated aqueous ammonia (50 ml) and extracted with diethyl ether. The extracts were dried with anhydrous sodium sulfate, evaporated and purified by column chromatography on silica gel (eluent, toluene?hexane, 1: 20). Three fractions were collected (in order of elution): 4,4'-di-tert-butylbiphenyl (34 mg), o-tert-butylnitrosobenzene (10 mg) and product 2 (183 mg, 81percent yield). For 2: white crystals, mp 86?88°C. 1H NMR (400 MHz, CDCl3) delta: 7.40 (dd, 1H, o-H, J 7.9 and 1.5 Hz), 7.28 (dd, 1H, o-H, J 7.9 and 1.5 Hz), 7.25?7.21 (m, 2H, p-H), 7.14 (ddd, 1H, o-H, J 7.9, 7.3 and 1.6 Hz), 7.01 (ddd, 1H, o-H, J 7.9, 7.3 and 1.5 Hz), 6.83?6.79 (m, 2H, p-H), 5.37 (s, 1H, 7-NH), 1.45 (s, 9H, But), 1.31 (s, 9H, But). 13C NMR (101 MHz, CDCl3) delta: 142.99 (p-C), 142.59 (o-C), 142.09 (o-C), 142.05 (p-C), 127.04 (o-C), 126.93 (o-C), 126.18 (p-C), 124.47 (o-C), 123.07 (o-C), 116.65 (p-C), 34.90 (CMe3), 34.19 (CMe3), 31.68 (CMe3), 30.70 (CMe3). ESI-HRMS, m/z: 228.2216 [M + H]+ (calc. for C20H28N, m/z: 282.2217).
  • 27
  • [ 3141-24-0 ]
  • [ 123324-71-0 ]
  • 3-bromo-2,5-bis(4-(tert-butyl)phenyl)thiophene [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate monohydrate; In tetrahydrofuran; water; for 24h;Inert atmosphere; Reflux; Synthesis of 3-bromo-2,5-bis(4-(tert-butyl)phenyl)thiophene: (30) Sodium carbonate monohydrate (58.0 g, 468 mmol) was dissolved in water (500 mL) and a solution of 4-(tert-butyl)-phenylboronic acid (40.0 g) and <strong>[3141-24-0]2,3,5-tribromothiophene</strong> (30.0 g, 94 mmol) in THF (500 mL) was added, and deoxygenated by bubbling with argon. Pd(PPh3)4 (5.0 g, 4.30 mmol) was added and the mixture refluxed for 24 h. The mixture was cooled and the aqueous phase separated and extracted with EtOAc. Organic fractions were combined washed with water (500 mL) and dried over MgSO4. The solvent was evaporated and the crude product washed in MeOH, filtered and dried overnight to afford a light yellow, powdery solid (35.46 g, 89%).
  • 29
  • [ 1034287-04-1 ]
  • [ 123324-71-0 ]
  • [ 98-09-9 ]
  • (E)-2-(4-(1-(4-(tert-butyl)phenyl)-2-(phenylsulfonyl)vinyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]
  • 30
  • [ 946-99-6 ]
  • [ 123324-71-0 ]
  • C21H24O4S [ No CAS ]
  • 31
  • [ 40299-87-4 ]
  • [ 123324-71-0 ]
  • C16H23NO4S [ No CAS ]
  • 33
  • [ 20357-21-5 ]
  • [ 123324-71-0 ]
  • C17H17NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); potassium carbonate; In toluene; at 120℃; for 12h;Green chemistry; Compound bromo-o-nitrobenzaldehyde (III) (0.229 g, 1.00 mmol) and 4-tert-butylphenylboronic acid (IV-1) (0.267 g, 1.5 mmol), Pd(dppf)Cl2 (73.1 mg, 0.1) Mm),K2CO3 (0.273 mg) and toluene (10 ml) were placed in a reaction flask, and the reaction was stirred under reflux at 120 ° C for 12 hours.After the reaction was completed, it was cooled to room temperature, and the reaction mixture was extracted with methylene chloride.The filtrate was concentrated under reduced pressure, and the obtained concentrate was subjected to silica gel column chromatography, with a mixture of petroleum ether and ethyl acetate at a volume ratio of 9:1 as an eluent.Collect the eluate containing the target compound, distill off the solvent and dry.The compound (V-1) was obtained in an amount of 0.170 g, a yield of 60percent, and a purity of ?98percent.
  • 34
  • [ 121554-10-7 ]
  • [ 123324-71-0 ]
  • 4-bromo-4’-(tert-butyl)-[1,1'-biphenyl]-2-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
82.0% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In N,N-dimethyl-formamide; at 120℃; for 24h;Inert atmosphere; 5-Bromo-2-iodo-benzonitrile (1.5 g, 5 mmol) under argon gas protection,tert-Butylbenzeneboronic acid (1.3 g, 7.5 mmol), K2CO3 (2.8 g, 20 mmol),Tetrakistriphenylphosphorus palladium (0.3g, 0.3mmol) and DMF (6mL) were added to a 30mL two-necked flask, reacted at 120 C for 24h, after TLC monitoring reaction was completed, cooled to room temperature, diluted with ethyl acetate 30mL, added 30mL water, stratified,The aqueous layer was extracted with ethyl acetate (25 mL×3).Purification by silica gel column (V ethyl acetate: V petroleum ether = 1: 20) afforded white solid 2-(4'-tert-butyl-phenyl)-5-bromo-benzonitrile (a1) 1.3 g, yield 82.0 %
82% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In N,N-dimethyl-formamide; at 120℃; for 2h;Inert atmosphere; General procedure: A mixture of (4-(tert-butyl)phenyl)boronic acid (7.5 mmol),K2CO3 (20 mmol), Pd[P(C6H5)3]4 (0.25 mmol), and compound 14(5 mmol) in DMF was stirred at 120 C for 24 h under an argonatmosphere. The reaction was diluted with H2O (30 mL) andextracted with ethyl acetate (20 mL 2). The organic phases werecombined, washed with brine (30 mL 3), dried over anhydrousNa2SO4, and concentrated under vacuum to yield the crude product,which was purified by flash column chromatography (0e10%ethyl acetate in petroleum ether). 4.1.15.1. 4-Bromo-4?-(tert-butyl)-[1, 10-biphenyl]-2-carbonitrile(15a). White solid (yield: 82%); 1H NMR (400 MHz, CDCl3)d 7.97e7.81 (m, 1H, ArH), 7.77e7.67 (m, 1H, ArH), 7.60e7.43 (m, 5H,ArH), 1.41e1.35 (m, 9H, eC6H4C(CH3)3).
  • 35
  • [ 3107-19-5 ]
  • [ 123324-71-0 ]
  • C26H28FNO2 [ No CAS ]
 

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