Реакция #43470

Уравнение реакции

4-chlorothiophenol

3-bromo-4-iodobenzotrifluoride

potassium tert-butoxide

2-bromo-4-trifluoromethyl-phenylamine

→

1-bromo-2-(4-chloro-phenylsulfanyl)-5-(trifluoromethyl)-benzene

Выход 81.0%

Растворители

toluene

Условия реакции

Обработка

1. 1
   Другоеat room temperature
2. 2
   Другое(rt)
3. 3
   Температураcooled to room temperature (rt)
4. 4
   Фильтрацияfiltered through celite
5. 5
   ДругоеThe solvent was evaporated off
6. 6
   Другоеthe crude product was purified by flash chromatography on silica gel (eluent: ethyl acetate/heptane 2:8)

Методика

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.

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