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

Participants

Reaction Steps

To a solution of 4-bromo-2-chlorobenzoic acid (2.00 g, 8.50 mmol) in DMF (20 ml) was added N,N-diisopropylethyl amine (3.18 ml, 18.69 mmol) followed by TBTU (3.00 g, 9.34 mmol) followed by dimethylhydroxylamine (829 mg, 8.50 mmol). The reaction mixture was stirred at rt overnight and then diluted with ether and the organic layer was washed with water, 1N HCl, sat. NaHCO3, and brine. The organic layer was then dried (MgSO4), filtered and concentrated in vacuo to give a residue which was purified by flash column chromatography to give 4-bromo-2-chloro-N-methoxy-N-methylbenzamide (2.27 g, 96%) as a colorless oil. 1H NMR (CDCl3, 300 MHz): δ 7.59 (d, J=1.5 Hz, 1H), 7.45 (dd, J=1.5, 8.0 Hz, 1H), 7.22 (d, J=8.0 Hz, 1H), 3.48 (br s, 3H), 3.38 (br s, 3H).

Provenance & Evidence