Sodium borohydride → 4-Bromo-2-fluoro-5-(hydroxymethyl)phenol

A solution of 2-bromo-4-fluoro-5-hydroxybenzaldehyde (2.0 g, 9.1 mmol) in MeOH (15 mL) was cooled in an ice bath before treatment of NaBH4 (390 mg, 10.3 mmol). After the complete addition of NaBH4, the reaction mixture was allowed to stir for 1 h at room temperature before it was quenched with equal volume of water. EtOAc (20 mL) was added to the reaction solution and the layers were separated. The aqueous layer was further extracted with equal volume of EtOAc before the organic layers were combined and dried over anhydrous Na2SO4 and filtered. The solvent was removed under reduced pressure. The residue was purified by silica gel column using Combiflash to give 4-bromo-2-fluoro-5-(hydroxymethyl)phenol (2.0 g, 83%).

1. customwas quenched with equal volume of water
2. additionEtOAc (20 mL) was added to the reaction solution
3. customthe layers were separated
4. extractionThe aqueous layer was further extracted with equal volume of EtOAc before the organic layers
5. dry with materialdried over anhydrous Na2SO4
6. filtrationfiltered
7. customThe solvent was removed under reduced pressure
8. customThe residue was purified by silica gel column

ORD record

ord-77c7c4b6a21f455097083c1d5dda53e7

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08716478B2