4-Methylmorpholine → 4-bromo-2-chloro-N-methoxy-N-methylbenzamide

Participants

Reaction Steps

A solution of 4-bromo-2-chloro-benzoic acid (3.30 g, 14 mmol), 2-chloro-4,6-dimethoxy-1,3,5-triazine (2.44 g, 14 mmol) and N-methylmorpholine in tetrahydrofuran were stirred for 2 hours at room temperature. N,O-Dimethylhydroxyamine hydrochloride (1.37 g, 14 mmol) and triethylamine (2 mL, 14 mmol) were added and the resulting mixture was stirred for 3 days. The reaction mixture was evaporated and ethyl acetate was added. The mixture was washed with 1N aqueous hydrochloric acid, water, brine, dried over sodium sulfate, filtered and concentrated in vacuo to give 4-bromo-2-chloro-N-methoxy-N-methyl-benzamide (3.52 g, 91%).

Provenance & Evidence