Hydrochloric Acid → 5-bromo-2-fluoro-N-methoxy-N-methylbenzamide

Participants

Reaction Steps

To a suspension of 20.0 g (91.3 mmol) 5-bromo-2-fluorobenzoic acid in 1 L CH2Cl2 was added 12.0 mL (137 mmol) oxalyl chloride and 3 drops of DMF. After stirring for 6 h, the reaction was concentrated by rotary evaporation, the residue was dissolved in 1 L of CH2Cl2, 11.6 g (119 mmol) N,O-dimethylhydroxylamine hydrochloride and 63.6 mL (456 mmol) triethylamine were added and the reaction was stirred overnight. The reaction was dumped into a separatory funnel with 1 M HCl, the layers were separated, the organic was washed with 1M NaOH, then water, dried over Na2SO4 and concentrated to provide 3-1 as a colorless oil. Data for 3-1: LC/MS: rt=1.76 min; m/z=262 (M+1).

Provenance & Evidence