p-Chlorothiophenol → 1-Bromo-2-(4-chlorophenylsulfanyl)-5-(trifluoromethyl)benzene

HRID 15192

反応式

HRID 15192 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:6][C:7]=1I.BrC1C=C(C(F)(F)F)C=CC=1N.[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([SH:32])=[CH:28][CH:27]=1.CC(C)([O-])C.[K+]>C1(C)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2OC2C=CC=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:6][C:7]=1[S:32][C:29]1[CH:30]=[CH:31][C:26]([Cl:25])=[CH:27][CH:28]=1

参加物

7

反応物 4

HCID 7815p-ChlorothiophenolHCID 938992-Bromo-4-trifluoromethylanilineHCID 162440892-Bromo-1-iodo-4-(trifluoromethyl)benzeneHCID 23665647Potassium tert-butoxide

生成物 1

HCID 686834131-Bromo-2-(4-chlorophenylsulfanyl)-5-(trifluoromethyl)benzene収率 81%

試薬・触媒・溶媒 2

HCID 4285986Bis[2-(diphenylphosphino)phenyl] ether触媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

To a stirred solution of tris(dibenzylidene)dipalladium(0) (Pd2dba3, 0.183 g, 0.2 mmol) and bis(2-diphenylphosphinophenyl)ether (DPEphos, 0.215 g, 0.2 mmol) in toluene (80 mL) was added 3-bromo-4-iodobenzotrifluoride (7.02 g, 20 mmol; prepared from 2-bromo-4-trifluoromethyl-phenylamine by diazotization according to the general procedure by Tunney and Stille J. Org. Chem. 1987, 52, 748-753), 4-chlorothiophenol (2.89 g, 20 mmol) and potassium tert-butoxide (2.46 g, 22 mmol) at room temperature (rt). The reaction mixture was stirred for 2.5 h at 100° C. and then cooled to room temperature (rt) and filtered through celite. The solvent was evaporated off and the crude product was purified by flash chromatography on silica gel (eluent: ethyl acetate/heptane 2:8) to produce 4.53 g (81%) of 1-bromo-2-(4-chloro-phenylsulfanyl)-5-(trifluoromethyl)-benzene as an oil.

後処理

  1. customat room temperature
  2. custom(rt)
  3. temperaturecooled to room temperature (rt)
  4. filtrationfiltered through celite
  5. customThe solvent was evaporated off
  6. customthe crude product was purified by flash chromatography on silica gel (eluent: ethyl acetate/heptane 2:8)

出典と根拠

ORDレコード
ord-d9347c96bc4843159a6b8f6dab67a98c
出典データセット
uspto-grants-2010_06
特許番号
US07732463B2

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