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[ CAS No. 2714-87-6 ]

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Chemical Structure| 2714-87-6
Chemical Structure| 2714-87-6
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Product Details of [ 2714-87-6 ]

CAS No. :2714-87-6 MDL No. :MFCD29066211
Formula : C13H9FO Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :200.21 g/mol Pubchem ID :-
Synonyms :

Safety of [ 2714-87-6 ]

Signal Word:Danger Class:8
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P310-P332+P313-P362-P403+P233-P405-P501 UN#:3261
Hazard Statements:H315-H318-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 2714-87-6 ]

  • Downstream synthetic route of [ 2714-87-6 ]

[ 2714-87-6 ] Synthesis Path-Downstream   1~24

  • 1
  • [ 1591-31-7 ]
  • [ 2714-87-6 ]
  • [ 398-36-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: copper / dimethyl sulfoxide / 12 h / 60 °C / Inert atmosphere 2: potassium carbonate / methanol; water / 2 h / 20 °C / Inert atmosphere 3: xenon fluoride / dichloromethane / 0.5 h / 20 °C / Inert atmosphere
  • 2
  • [ 73789-98-7 ]
  • [ 2714-87-6 ]
  • [ 398-36-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / methanol; water / 2 h / 20 °C / Inert atmosphere 2: xenon fluoride / dichloromethane / 0.5 h / 20 °C / Inert atmosphere
  • 3
  • [ 73790-13-3 ]
  • [ 2714-87-6 ]
  • [ 398-36-7 ]
YieldReaction ConditionsOperation in experiment
1: 23 %Spectr. 2: 11 %Spectr. With xenon fluoride In dichloromethane at 20℃; for 0.5h; Inert atmosphere;
  • 4
  • [ 92-92-2 ]
  • [ 2714-87-6 ]
YieldReaction ConditionsOperation in experiment
94% With sodium flouride; N-(difluoro-λ4-sulfanylidene)-N-ethylethanaminium tetrafluoroborate In ethyl acetate at 20℃; for 24h; Inert atmosphere;
92% With dmap; trifluoromethyl trifluoromethanesulfonate In dichloromethane at 20℃; for 0.25h; Inert atmosphere; Schlenk technique;
73% With [bis(2-methoxyethyl)amino]-sulfur trifluoride In dichloromethane at 0℃; for 0.0833333h; Inert atmosphere; 1-3. Procedures of preparation of acyl fluoride 1 General procedure: Method AS3: Under N2 atmosphere, the corresponding carboxylic acid (3.00 mmol) was transferredto a PFA bottle equipped with a stirrer bar. After addition of CH2Cl2 (5.00 mL) to the bottle, the reactionmixture was cooled at 0 °C in ice bath. Then, Deoxo-fluor (0.560 mL, 3.04 mmol) was added to thesolution. The bottle was capped, and the reaction mixture was stirred at 0 °C for 5-30 min (written ateach substrate in parentheses). The reaction was quenched by addition of aqueous NaHCO3. Themixture was extracted with CH2Cl2 (10.0 mL) three times. The combined organic layer was dried overNa2SO4. Solvents were removed under reduced pressure. The crude material was purified by silica gelcolumn chromatography (hexane/AcOEt = 97:3) to give the corresponding acid fluoride.
65% With triethylamine trishydrofluoride; N-(difluoro-λ4-sulfanylidene)-N-ethylethanaminium tetrafluoroborate In dichloromethane at 25℃; for 2h;
53% With trichloroisocyanuric acid; caesium fluoride In acetonitrile at 20℃; for 24h; Inert atmosphere; Sealed tube;
99 %Spectr. With 2,12-di-tert-butyl-7,8-dihydro-6H-dipyrido[1,2-a:2',1'-c][1,4]diazepine-5,9-diium fluoride pentafluorosulfide In N,N-dimethyl-formamide at 90℃; Schlenk technique;
Multi-step reaction with 2 steps 1: thionyl chloride; N,N-dimethyl-formamide / toluene / 4 h / 75 °C / Sealed tube 2: Palladium(0) bis(dibenzylideneacetone); (S)-Cl,MeO-BIPHEP / 1,4-dioxane / 1 h / 23 °C / Inert atmosphere; Sealed tube
Stage #1: biphenyl-4-carboxylic acid In dichloromethane at 0℃; for 0.5h; Schlenk technique; Stage #2: With [bis(2-methoxyethyl)amino]-sulfur trifluoride In dichloromethane at 0℃; for 0.5h; Schlenk technique; 3.2.2. Representative Procedure for the Synthesis of Acyl Fluorides from Carboxylic Acids General procedure: To a 20 mL of Schlenk tube charged with a magnetic stir bar, were successively added carboxylic acid (3.0 mmol) and CH2Cl2 (15 mL). After the mixture was stirred at 0 °C for 30 min, Deoxo-Fluorreagent (608 L, 3.3 mmol, 1.1 equiv) was slowly added to the reaction mixture. After the reaction mixture was stirred at 0 °C for 30 min, the solution was slowly poured into saturated NaHCO3,extracted with CH2Cl2 (3 15 mL), and dried over MgSO4. The crude product was purified by flash chromatography on silica gel to aord the corresponding acyl fluorides 1 [36].
With N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate In tetrahydrofuran at 20℃;
With N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate In tetrahydrofuran at 20℃; Inert atmosphere; Glovebox;
90 %Spectr. With pyridine; thionyl fluoride In dichloromethane at 20℃; for 0.5h;
With N-ethyl-N,N-diisopropylamine; fluoro-N,N,N′,N′-bis(tetramethylene)formamidinium hexafluorophosphate In dichloromethane at 23℃; for 0.5h; Sealed tube; Inert atmosphere;

Reference: [1]Gonay, Marie; Batisse, Chloé; Paquin, Jean-François [Journal of Organic Chemistry, 2020, vol. 85, # 15, p. 10253 - 10260]
[2]Song, Hai-Xia; Tian, Ze-Yu; Xiao, Ji-Chang; Zhang, Cheng-Pan [Chemistry - A European Journal, 2020, vol. 26, # 69, p. 16261 - 16265]
[3]Ishida, Naoyoshi; Iwamoto, Hiroaki; Sunagawa, Denise Eimi; Ohashi, Masato; Ogoshi, Sensuke [Synthesis, 2021, vol. 53, # 17, p. 3137 - 3143]
[4]Keaveney, Sinead T.; Schoenebeck, Franziska [Angewandte Chemie - International Edition, 2018, vol. 57, # 15, p. 4073 - 4077][Angew. Chem., 2018, vol. 130, # 15, p. 4137 - 4141,5]
[5]Liang, Yumeng; Zhao, Zhengyu; Taya, Akihito; Shibata, Norio [Organic Letters, 2021, vol. 23, # 3, p. 847 - 852]
[6]Rueping, Magnus; Nikolaienko, Pavlo; Lebedev, Yury; Adams, Alina [Green Chemistry, 2017, vol. 19, # 11, p. 2571 - 2575]
[7]Pan, Fei; Boursalian, Gregory B.; Ritter, Tobias [Angewandte Chemie - International Edition, 2018, vol. 57, # 51, p. 16871 - 16876][Angew. Chem., 2018, vol. 130, p. 17113 - 17118,6]
[8]Wang, Xiu; Wang, Zhenhua; Liu, Li; Asanuma, Yuya; Nishihara, Yasushi [Molecules, 2019, vol. 24, # 9]
[9]Malapit, Christian A.; Bour, James R.; Brigham, Conor E.; Sanford, Melanie S. [Nature, 2018, vol. 563, # 7729, p. 100 - 104]
[10]Malapit, Christian A.; Bour, James R.; Laursen, Simon R.; Sanford, Melanie S. [Journal of the American Chemical Society, 2019, vol. 141, # 43, p. 17322 - 17330]
[11]Lee, Cayo; Sammis, Glenn M.; Thomson, Brodie J. [Chemical Science, 2022, vol. 13, # 1, p. 188 - 194]
[12]Scott, Jason A.; Soto-Velasquez, Monica; Hayes, Michael P.; Lavigne, Justin E.; Miller, Heath R.; Kaur, Jatinder; Ejendal, Karin F. K.; Watts, Val J.; Flaherty, Daniel P. [Journal of Medicinal Chemistry, 2022, vol. 65, # 6, p. 4667 - 4686]
  • 5
  • [ 1082207-38-2 ]
  • [ 2714-87-6 ]
  • [ 73183-34-3 ]
  • C31H35BO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With 1,1'-bis-(diphenylphosphino)ferrocene; copper diacetate; sodium trimethylsilanolate In tetrahydrofuran at 0℃; for 3h; regioselective reaction;
  • 6
  • [ 1082207-38-2 ]
  • [ 2714-87-6 ]
  • C32H27F3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: copper diacetate; 1,1'-bis-(diphenylphosphino)ferrocene; sodium trimethylsilanolate / tetrahydrofuran / 3 h / 0 °C 2: tetrakis(triphenylphosphine) palladium(0); caesium carbonate / 1,2-dimethoxyethane / 20 h / 60 °C
  • 7
  • [ 2714-87-6 ]
  • [ 120120-26-5 ]
  • [ 398-36-7 ]
YieldReaction ConditionsOperation in experiment
40% With potassium phosphate; [PdCl(cinnamyl)]2; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene at 170℃; for 16h;
37 mg With potassium phosphate; bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene at 170℃; for 16h; Inert atmosphere; Sealed tube;
  • 8
  • [ 2714-87-6 ]
  • [ 81290-20-2 ]
  • [ 398-36-7 ]
YieldReaction ConditionsOperation in experiment
With potassium phosphate; bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene at 160℃; for 16h; Sealed tube;
  • 9
  • [ 2714-87-6 ]
  • [ 92-52-4 ]
YieldReaction ConditionsOperation in experiment
70% With triethylsilane; palladium diacetate; tricyclohexylphosphine; 1,2-bis-(dicyclohexylphosphino)ethane In toluene at 100℃; for 20h; Inert atmosphere; Sealed tube;
  • 10
  • [ 2714-87-6 ]
  • [ 3218-36-8 ]
YieldReaction ConditionsOperation in experiment
84% With triethylsilane; palladium diacetate; tricyclohexylphosphine In toluene at 100℃; for 20h; Inert atmosphere; Sealed tube;
  • 11
  • [bis(difluoromethyl)zinc(dmpu)2] [ No CAS ]
  • [ 14002-51-8 ]
  • [ 2714-87-6 ]
YieldReaction ConditionsOperation in experiment
28 %Spectr. With (S)-(-)-5,5'-dichloro-6,6'-dimethoxy-2,2'-bis(diphenylphosphino)-1,1'-biphenyl; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane at 23℃; for 1h; Inert atmosphere; Sealed tube;
  • 13
  • [ 14002-51-8 ]
  • [ 2714-87-6 ]
YieldReaction ConditionsOperation in experiment
75% With potassium hydrogen difluoride; tetra-n-butyl-ammonium chloride; lithium hydroxide monohydrate In dichloromethane at 20℃; for 16h; Preparation of Acyl Fluorides 2; General Procedure General procedure: A 250 mL round-bottomed flask was charged with potassium bifluoride(15.62 g, 200 mmol) and water (40.17 g), and stirred at ambienttemperature for 1 h. Then tetrabutylammonium chloride (0.279 g, 1.0mmol, 1 mol%), DCM (used in two-fold volume of acyl chloride) andacyl chloride (1a-y; 100 mmol) were added, and the mixture wasstirred (1400 rpm) with a magnetic bar (fish; 15 × 33 mm) at r.t. forthe time given in the characterization data. The mixture was thentransferred to a separatory funnel, separated, and the aqueous phasewas extracted with DCM (50 mL). The combined organic phases werewashed with brine (50 mL), and dried with MgSO4. The mixture wasfiltered and evaporated, and the residue was distilled under reducedpressure to obtain product 2a-y.
68% With potassium fluoride; 18-crown-6 ether In tetrahydrofuran at 40℃; for 24h; Schlenk technique; Inert atmosphere;
47% With potassium fluoride In acetonitrile at 20℃; for 72h; Inert atmosphere;
With potassium fluoride; 18-crown-6 ether In tetrahydrofuran at 40℃; for 24h; Schlenk technique; 3.2.1. Representative Procedure for the Synthesis of Acyl Fluorides from Acyl Chlorides General procedure: To a 50 mL of Schlenk tube charged with a magnetic stir bar, were successively added acyl chloride(4.0 mmol), 18-crown-6 (52.9 mg, 0.2 mmol, 5 mol %), KF (2.32 g, 40 mmol, 10 equiv), and THF (20 mL).After the reaction was stirred at 40 °C for 24 h, insoluble inorganic solid (KF or KCl) was filtered,and the volatiles were concentrated using a rotary evaporator. The crude product was purified by bulb-to-bulb distillation to aord the corresponding acyl fluorides 1 [35].
With potassium fluoride; 18-crown-6 ether In tetrahydrofuran at 40℃; for 24h; Schlenk technique; Inert atmosphere;
With caesium fluoride In acetonitrile at 60℃;
With potassium fluoride; 18-crown-6 ether In tetrahydrofuran at 40℃; for 24h; Schlenk technique; Inert atmosphere;
Multi-step reaction with 2 steps 1: triethylamine; 4‐dimethylaminopyridine / dichloromethane / 0 - 20 °C / Inert atmosphere 2: 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo-[2.2.2]octane bis(tetrafluoroborate); [1,1'-bis(diphenylphosphino)ferrocene]nickel(II) chloride / 1,2-dichloro-ethane / 18 h / 130 °C / Schlenk technique; Inert atmosphere
Multi-step reaction with 2 steps 1: triethylamine / N,N-dimethyl acetamide / 0 - 20 °C / Inert atmosphere 2: triethylamine trishydrofluoride / Isopropyl acetate / 2 h / 25 °C / Green chemistry

  • 14
  • [ 1006-68-4 ]
  • [ 2714-87-6 ]
  • C22H15NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; triphenylphosphine; copper(l) chloride In toluene at 80℃; for 24h; Glovebox; Sealed tube;
  • 15
  • [ 2714-87-6 ]
  • [ 17955-46-3 ]
  • [ 51533-89-2 ]
YieldReaction ConditionsOperation in experiment
82% With cesium fluoride; nickel dichloride; In toluene; at 140℃; for 24h;Schlenk technique; Inert atmosphere; General procedure: A 20 mL dried Schlenk tube containing a stirring bar and CsF (60.8 mg, 0.4 mmol, 2 equiv) was dried with a heat gun under reduced pressure and filled with Ar after cooling to room temperature. To this vessel, were added NiCl2 (1.3 mg, 0.01 mmol, 5 mol %), toluene (1 mL), acyl fluorides (1) (0.2 mmol,1 equiv) and <strong>[17955-46-3]trimethyl(tributylstannyl)silane</strong> (2) (87.2 mg, 0.24 mmol, 1.2 equiv). The mixture was heated at 140 C with stirring for 24 h. The solution was then cooled to room temperature, and the solvent was removed under vacuum. The decarbonylative stannylation products 3 were purified by flash column chromatography on silica gel.
  • 16
  • [ 2714-87-6 ]
  • [ 75-24-1 ]
  • [ 34352-84-6 ]
YieldReaction ConditionsOperation in experiment
92% With bis-diphenylphosphinomethane In toluene at 120℃; for 24h; Schlenk technique; Inert atmosphere;
  • 17
  • [ 2714-87-6 ]
  • [ 97-93-8 ]
  • [ 41658-01-9 ]
  • 4-(pentan-3-yl)-1,1'-biphenyl [ No CAS ]
  • (E)-4-(pent-2-en-3-yl)-1,1'-biphenyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
13% With bis-diphenylphosphinomethane In toluene at 120℃; for 24h; Schlenk technique; Inert atmosphere;
  • 18
  • [ 2714-87-6 ]
  • [ 5720-07-0 ]
  • [ 13041-66-2 ]
YieldReaction ConditionsOperation in experiment
With bis(1,5-cyclooctadiene)nickel (0); diphenyl(methyl)phosphine In tetrahydrofuran at 100℃; for 16h; Inert atmosphere; Glovebox;
  • 19
  • [ 59409-55-1 ]
  • [ 2714-87-6 ]
  • [ 73183-34-3 ]
  • C30H33BO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With C37H36FeNOPS; copper diacetate; sodium trimethylsilanolate In tetrahydrofuran at 0℃; for 4h; enantioselective reaction;
  • 20
  • [ 745783-97-5 ]
  • [ 2714-87-6 ]
  • [ 18057-71-1 ]
YieldReaction ConditionsOperation in experiment
81% With copper (II)-fluoride; potassium fluoride; bis(1,5-cyclooctadiene)nickel (0); triphenylphosphine In toluene at 150℃; for 24h; Schlenk technique; Inert atmosphere;
  • 21
  • [ 2714-87-6 ]
  • [ 201733-56-4 ]
  • [ 5123-05-7 ]
YieldReaction ConditionsOperation in experiment
40 mg With C42H71FNiP2 In tetrahydrofuran at 115℃; for 16h; Inert atmosphere; Sealed tube; chemoselective reaction;
  • 22
  • [ 2714-87-6 ]
  • [ 661-69-8 ]
  • [ 1625-95-2 ]
YieldReaction ConditionsOperation in experiment
77% With 1,4-bis(dicyclohexylphosphino)butane; palladium dichloride In o-xylene at 140℃; for 10h; Inert atmosphere; Schlenk technique;
  • 23
  • [ 25327-57-5 ]
  • [ 2714-87-6 ]
YieldReaction ConditionsOperation in experiment
52% With benzoyl fluoride; 1,4-di(diphenylphosphino)-butane; bis(dibenzylideneacetone)-palladium(0) In toluene at 120℃; for 24h; Inert atmosphere; Glovebox; Sealed tube;
  • 24
  • [ 2714-87-6 ]
  • [ 81290-20-2 ]
  • [ 2369-31-5 ]
  • 2-([1,1’-biphenyl]-4-yl)-1,1,1,3,3,3-hexafluoropropan-2-yl [1,1’-biphenyl]-4-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium fluoride; Trimethyl borate In 1,4-dioxane at 80℃; for 2h; Inert atmosphere; Sealed tube;
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