Water → 4-Bromo-N-methoxy-N-methylbenzamide

Participants

Reaction Steps

To a solution of 4-bromobenzoyl chloride (12.43 g, 56.6 mmol) and N,O-dimethyl hydroxyamine hydrochloride (8.29 g, 85.0 mmol) in CH2Cl2 (200 ml) was added triethylamine (23.7 ml, 170 mmol) at 0° C. The mixture was stirred at room temperature for 2 hours. Water (200 ml) was added and the aqueous layer was extracted with CH2Cl2 (150 ml×2). The combined organic layer was washed with 2N HCl (200 ml), saturated aqueous NaHCO3 (200 ml), and brine (200 ml), dried over Na2SO4, and concentarated in vacuo to give 14.9 g (quant.) of the title compound as a white solid.

Provenance & Evidence