Boron tribromide → 6-Bromo-2,3-dihydroxybenzaldehyde

Participants

Reaction Conditions

Reaction Steps

6-Bromo-2-hydroxy-3-methoxybenzaldehyde (2.00 g, 8.65 mmol) was dissolved in methylene chloride (10 mL) and cooled to 0° C. Boron tribromide (17.0 mL of a 1.0 M solution, 17.00 mmol) was added by syringe and the solution was stirred at 0° C. for 1 h before allowing the reaction to warm up to ambient temperature and stir for 15 h at which time TLC analysis indicated the reaction complete. The reaction mixture was poured onto ice and extracted with ethyl acetate. The organic layers were dried with magnesium sulfate and concentrated by rotary evaporation to afford 1.82 g of 6-bromo-2,3-dihydroxybenzaldehyde (8.39 mmol, 97% yield) as a yellow solid.

Provenance & Evidence