2-Bromo-5-hydroxybenzaldehyde → 4-bromo-3-(hydroxymethyl)phenol

To a solution of 4-bromo-3-formylphenol (20.1 g, 100 mmol) in methanol (200 mL) was added sodium borohydride (1.90 g, 50.0 mmol) portionwise at 0° C., and the mixture was stirred at room temperature for 1 h. The solvent was removed under reduced pressure to a half volume, 6 M HCl (50 mL) was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried on anhydrous sodium sulfate. The solvent was removed under reduced pressure to give 4-bromo-3-hydroxymethylphenol (19.4 g, 96%).

1. customThe solvent was removed under reduced pressure to a half volume, 6 M HCl (50 mL)
2. additionwas added
3. extractionthe mixture was extracted with ethyl acetate
4. washThe organic layer was washed with brine
5. dry with materialdried on anhydrous sodium sulfate
6. customThe solvent was removed under reduced pressure

ORD record

ord-9c9a5e2af6b647f59fd00bdb7984e216

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08461135B2