1,4-Dibromobenzene → 1-(4-Bromophenyl)-2,2-difluoroethan-1-one

Participants

Reaction Conditions

Reaction Steps

n-Butyllithium (1.6 M in hexane) (165 mL, 0.264 mmol) was added dropwise to a −78° C. solution of 1,4-dibromobenzene (60.1 g) in diethyl ether (500 mL). After stirring at −78° C. for 2 h, ethyl trifluoroacetate (40 g) was added dropwise and the mixture was allowed to warm to ambient temperature overnight. The reaction mixture was cooled to −20° C., quenched with saturated aqueous ammonium chloride and extracted with ether. The combined organic phases were washed with saturated aqueous sodium bicarbonate, dried (sodium sulfate) and concentrated in vacuo. Chromatography over silica eluting with petroleum ether/ethyl acetate (20:1) afforded the title compound.

Provenance & Evidence