Reacción #72467

Ecuación de reacción

water

sodium hydroxide

water

methyl 2-amino-5-bromobenzoate

lithium aluminium hydride

→

(2-amino-5-bromophenyl)methanol

Rendimiento 59.8%

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Filtraciónwas filtered through celite
2. 2
   OtroEvaporation of the solvent and purification of the crude product by flash chromatography on silica gel (dichloromethane/ethyl acetate, 2/1)

Procedimiento

To a suspension of lithium aluminium hydride (0.33 g, 8.7 mmol) in THF (10 ml) was added a solution of methyl 2-amino-5-bromobenzoate (2.0 g, 8.7 mmol) in 20 ml THF at 0° C. under nitrogen. Then stirring was continued for 2 h. 0.64 ml water, 2 M solution of sodium hydroxide (0.64 ml) and again 1.28 ml water were added before the resulting mixture was filtered through celite. Evaporation of the solvent and purification of the crude product by flash chromatography on silica gel (dichloromethane/ethyl acetate, 2/1) yielded (2-amino-5-bromophenyl)methanol (1.0 g, 5.2 mmol, 59%) as off-white solid.

Fuente