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

HRID 15192

Reaktionsgleichung

Reaktionsgleichung von HRID 15192
[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

Komponenten

7

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 4285986Bis[2-(diphenylphosphino)phenyl] etherKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-d9347c96bc4843159a6b8f6dab67a98c
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732463B2

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