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

Temperature

0 °C

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.

1. customthe reaction
2. temperatureto warm up to ambient temperature
3. stirringstir for 15 h at which time TLC analysis
4. additionThe reaction mixture was poured onto ice
5. extractionextracted with ethyl acetate
6. dry with materialThe organic layers were dried with magnesium sulfate
7. concentrationconcentrated by rotary evaporation

ORD record

ord-b4f0ffe745404e8e915ec68940ea06fe

Source dataset

uspto-grants-1999_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05948817