4-bromo-2-chloro-N-methoxy-N-methylbenzamide → 1-(4-Bromo-2-chlorophenyl)ethan-1-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-bromo-2-chloro-N-methoxy-N-methylbenzamide (2.27 g, 8.15 mmol) in THF at −78° C. was added methylmagnesium chloride (4.07 ml, 3M solution in THF, 12.23 mmol) dropwise. The reaction mixture was stirred at −78° C. for 1 h and then warmed to rt slowly and stirring was continued at rt overnight. The reaction mixture was quenched with 1N HCl and extracted with ether. The organic layer was washed with water, and brine, dried (MgSO4), filtered and concentrated in vacuo to give a residue which was purified by flash column chromatography (1:4 ether:pentane) to give 1-(4-bromo-2-chlorophenyl)-ethanone (1.52 g, 80%) as a yellow oil. 1H NMR (CDCl3, 300 MHz): δ 7.61 (m, 1H), 7.50-7.44 (m, 2H), 2.64 (s, 3H).

Provenance & Evidence