Triethylamine → 2-Bromo-3,4-dimethoxybenzonitrile

Participants

Reaction Steps

A mixture of hydroxylamine hydrochloride (1.42 g, 20. 4 mmol) and triethylamine (5.7 ml, 40.8 mmol) in acetonitrile (10 ml) was stirred at room temperature for 15 minutes before a solution of 2-bromo-3,4-dimethoxybenzaldehyde (5.0 g, 20.4 mmol) in acetonitrile (40 ml) was added over 40 minutes. The resulting mixture was stirred overnight before a fifth of the resulting solution was charged with methanesulfonyl chloride (0.74 ml, 10 mmol total) and triethylamine (0.6 ml, 4.3 mmol total) portionwise over 6 hours. The mixture was stirred overnight, quenched with water, extracted with ethyl acetate, dried over MgSO4 and concentrated in-vacuo to give 0.90 g of the subtitle product (93%).

Provenance & Evidence