Boron tribromide → HCID 23043622, compound

Participants

Reaction Conditions

Reaction Steps

A dichloromethane (40 ml) solution of 4-chloro-N-[4-[2-(3,4-dimethoxyphenyl)ethyl]phenyl]-2-hydroxybenzamide (0.50 g, 1.21 mmol) is cooled to -78° C. under an argon atmosphere. Boron tribromide (1.0M solution in dichloromethane, 5.5 ml, 5.5 mmol) is added, and the mixture is stirred at -78° C. for four hours, followed by stirring at ambient temperature for two hours. The solution is then recooled to -20° C. and quenched with water (5.5 ml). The mixture is allowed to stir at ambient temperature for 12 hours, after which additional water (10 ml) is added. Filtration affords 4-chloro-N-[4-[2-(3,4-dihydroxyphenyl)ethyl]phenyl]-2-hydroxybenzamide (0.42 g, 91%), mp 229°-213° C. after recrystallization from methanol/water.

Provenance & Evidence