2-Amino-5-bromobenzoic acid → 2-Amino-5-bromobenzenemethanol

To a solution of 2-amino-5-bromobenzoic acid (10.0 g, 46.3 mmol) in THF (150 mL) was added BH3-THF (1 M, 231 mL) at room temperature, and the reaction mixture was stirred overnight. An aliquot of the reaction mixture was analyzed by LCMS and indicated that the reaction had proceeded to completion. The reaction was quenched with water (150 mL) and extracted with EtOAc (3×500 mL). The organic layers were separated, combined, washed with water (200 mL) and brine (200 mL), dried over sodium sulfate, filtered, and concentrated to afford the title compound (10 g, crude), which was directly used in the next step without further purification. MS (ES+) C7H8BrNO requires: 201. Found: 202, 204 [M+H]+.

1. customThe reaction was quenched with water (150 mL)
2. extractionextracted with EtOAc (3×500 mL)
3. customThe organic layers were separated
4. washwashed with water (200 mL) and brine (200 mL)
5. dry with materialdried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated

ORD record

ord-9651fc98adb342a09dbfb9a3dbc384b4

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09126951B2