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

HRID 15192

반응식

HRID 15192 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 4285986Bis[2-(diphenylphosphino)phenyl] ether촉매HCID 1140Toluene용매

반응 조건

온도
100 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-d9347c96bc4843159a6b8f6dab67a98c
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732463B2

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