Dimethyl Sulfoxide → 2-Bromo-4-fluorobenzaldehyde

Participants

Reaction Conditions

Reaction Steps

To a −78° C. cooled solution of oxalyl chloride (8.43 ml; 96.58 mmol) in anhydrous dichloromethane (300 ml) was added dropwise dimethyl sulfoxide (13.71 ml; 193.16 mmol). The mixture was stirred at −78° C. for 5 minutes then a solution of (2-bromo-4-fluorophenyl)methanol (Description 77, 18 g; 87.8 mmol) in anhydrous dichloromethane (150 ml) was added slowly. The resulting mixture was stirred at −78° C. for 15 minutes then triethylamine (36.71 ml; 263.4 mmol) was added and the mixture allowed to warm to room temperature over 1 hour. The mixture was washed with water (2×500 ml), saturated NaCl (200 ml), dried over Na2SO4, filtered through a 2 inch plug of silica gel and evaporated to give the title compound (16 g, 89%) as a white solid.

Provenance & Evidence