Reacción #84726

Ecuación de reacción

2-amino-5-bromo-3-chlorobenzoic acid

borohydride

→

title product

Rendimiento 82.0%

(2-amino-5-bromo-3-chlorophenyl)methanol

Rendimiento 82.0%

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe mixture was quenched with methanol (100 mL)
2. 2
   Concentraciónconcentrated to a volume of 50 mL
3. 3
   workup.ADDITIONThe residue was diluted with aqueous sodium bicarbonate (400 mL)
4. 4
   Extracciónextracted with ethyl acetate (200 mL×3)
5. 5
   OtroThe organic layers were separated
6. 6
   Lavadowashed by brine (100 mL)
7. 7
   Secadodried over sodium sulfate
8. 8
   Filtraciónfiltered
9. 9
   Concentraciónconcentrated

Procedimiento

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]+.

Fuente