Borohydride → (2-Amino-5-bromo-4-chlorophenyl)methanol

To a solution of 2-amino-5-bromo-4-chlorobenzoic acid (9.0 g, 36.0 mmol) in THF (150 mL) was added borohydride in THF (144 mL, 1 M) at room temperature, and the reaction mixture was stirred overnight. The reaction mixture was quenched with methanol (50 mL), and concentrated to a volume of 50 mL. The residue was diluted with water (100 mL) and extracted with ethyl acetate (150 mL×3). The organic layers were separated, combined, washed with water (100 mL) and brine (100 mL), dried over sodium sulfate, filtered and concentrated to afford the title compound (crude, 6 g, 71%).

1. customThe reaction mixture was quenched with methanol (50 mL)
2. concentrationconcentrated to a volume of 50 mL
3. additionThe residue was diluted with water (100 mL)
4. extractionextracted with ethyl acetate (150 mL×3)
5. customThe organic layers were separated
6. washwashed with water (100 mL) and brine (100 mL)
7. dry with materialdried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-077a42d133124a1b9775569963818e3b

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09434700B2