1,2-Dichloroethane → 4-Bromo-3-fluoro-N-methoxy-N-methylbenzamide

Participants

Reaction Steps

N,O-Dimethylhydroxylamine (2.45 g, 25.1 mmol) was added to an ambient temperature solution of 4-bromo-3-fluorobenzoic acid (5 g, 22.8 mmol), EDC (5.25 g, 27.4 mmol), HOBt (4.2 g, 27.4 mmol) and NMM (12.55 mL, 114.2 mmol) in methylene chloride (50 mL). After stirring at ambient temperature overnight, the reaction mixture was poured into ethyl acetate and washed successively with saturated aqueous sodium bicarbonate and brine, dried (sodium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 40-80% ethyl acetate/hexane afforded 4-bromo-3-fluoro-N-methoxy-N-methylbenzamide.

Provenance & Evidence