Dimethyl Sulfoxide → 5-Bromo-2-chlorobenzaldehyde

Participants

Reaction Steps

18 ml (0.26 mol) of DMSO are introduced into 64 ml of dichloromethane and, at −78° C., 16.1 g (0.127 mol, 11.1 ml) of oxalyl chloride are added. After 30 min, a solution of 13.1 g (59 mmol) of (5-bromo-2-chlorophenyl)methanol in 100 ml of chloroform is added dropwise. After 20 min, 40 ml of triethylamine are added and the reaction mixture is slowly warmed to RT. After the addition of 50 ml of water the mixture is extracted several times with ethyl acetate. The combined organic phases are washed successively with 2N hydrochloric acid, water, a saturated sodium bicarbonate solution and a saturated sodium chloride solution. The organic phase is dried over magnesium sulfate and concentrated in vacuo. The resulting solid is dried Yunder high vacuum to constant weight.

Provenance & Evidence