Borohydride → (2-Amino-5-bromo-3-chlorophenyl)methanol

To a solution of 2-amino-5-bromo-3-chlorobenzoic acid (13.0 g, 52.0 mmol) in THF (200 mL) was added borohydride in THF (300 mL, 1N) at ice/water bath, and the reaction mixture was stirred at room temperature overnight. The mixture was quenched with methanol (100 mL) and concentrated to a volume of 50 mL. The residue was diluted with aqueous sodium bicarbonate (400 mL) and extracted with ethyl acetate (200 mL×3). The organic layers were separated, combined, washed by brine (100 mL), dried over sodium sulfate, filtered and concentrated to afford the title product (10.0 g, 82%). MS (ES+) C7H7BrClNO requires: 234, 236, found: 236, 238 [M+H]+.

1. customThe mixture was quenched with methanol (100 mL)
2. concentrationconcentrated to a volume of 50 mL
3. additionThe residue was diluted with aqueous sodium bicarbonate (400 mL)
4. extractionextracted with ethyl acetate (200 mL×3)
5. customThe organic layers were separated
6. washwashed by brine (100 mL)
7. dry with materialdried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-2c837e710ae1411eb1a34020b955fe70

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09434700B2