Boron tribromide → 4-((5-Bromo-2-chlorophenyl)methyl)phenol

Participants

Reaction Conditions

Reaction Steps

4-bromo-1-chloro-2-(4-methoxybenzyl)-benzene (10 g, 32 mmol) was dissolved in dichloromethane (32 mL) and cooled to 0° C. under nitrogen. A 1.0 M boron tribromide solution in dichloromethane (35.3 mL, 34.3 mmol) was added dropwise over 10 minutes. Following the addition, the ice bath was removed and the solution was stirred at room temperature for 1 hour. The reaction mixture was cooled to 0° C. and quenched by addition of 1N aqueous hydrochloric acid solution (45 mL). The mixture was stirred for 30 minutes, transferred to a separatory funnel, the organic layer was collected, and the aqueous layer was extracted with dichloromethane (45 mL). The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 4-(5-bromo-2-chlorobenzyl)phenol (9.5 g, 99% yield) as a white solid.

Provenance & Evidence