Pyridine → 4-bromo-N-methoxy-N,3-dimethylbenzamide

Participants

Reaction Steps

A stirred suspension of 4-bromo-3-methylbenzoic acid (5.0 g, 0.023 mole) in thionyl chloride (20 ml) was heated under reflux for 2 hours, then concentrated in vacuo. The residual acid chloride was dissolved in dichloromethane (100 ml) and added dropwise over 10 minutes to a stirred solution of N,O-dimethylhydroxylamine hydrochloride (2.4 g, 0.025 mole) and pyridine (5.6 ml, 0.069 mole) in dichloromethane (150 ml) and acetonitrile (20 ml) at -20° C. The reaction mixture was allowed to warm to room temperature over 3 hours then treated with 10% Na2CO3 solution and extracted with dichloromethane. The extract was dried (Na2SO4) and concentrated in vacuo to afford the title compound as a pale yellow oil (5.9 g, 100%).

Provenance & Evidence