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

HRID 15192
Notes
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Reaction equation

HRID 15192 reaction equation
[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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 4285986
Bis[2-(diphenylphosphino)phenyl] ether
Catalyst
HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-d9347c96bc4843159a6b8f6dab67a98c
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07732463B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes