3-Bromophenol → 1-Bromo-3-(2,2,2-trifluoroethoxy)benzene

Participants

Reaction Conditions

Reaction Steps

To a solution of 2,2,2-trifluoroethyl 4-methylbenzenesulfonate (3 g, 11.81 mmol) in dimethylformamide (20 mL) was added 3-bromophenol (1 g, 5.78 mmol) and NaOH (500 mg, 12.50 mmol). The resulting solution was stirred at 100° C. for 3 h. The reaction mixture was quenched by the adding H2O (100 mL) and extracted with methylene chloride (3×50 mL). The combined organic layers were dried (Na2SO4) and concentrated, and the residue purified by silica gel column chromatography (1:20 EtOAc/petroleum ether) to provide 1.1 g (31%) of 1-bromo-3-(2,2,2-trifluoroethoxy)benzene.

Provenance & Evidence