Reacción #74462

Ecuación de reacción

5-bromo-2-chlorobenzoic acid

compound 3

5-bromo-2-chlorobenzoic acid

→

title compound

5-Bromo-2-chlorobenzyl alcohol

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturare-cooled to 0° C.
2. 2
   Otroquenched with methanol
3. 3
   workup.ADDITIONThe mixture was diluted with water
4. 4
   Extracciónextracted with ethyl acetate
5. 5
   LavadoThe organic layer was washed with brine
6. 6
   Secadodried over magnesium sulfate
7. 7
   Filtraciónfiltered
8. 8
   Otroevaporated in vacuo

Procedimiento

To a solution 5-bromo-2-chlorobenzoic acid (compound 3, 100 g, 425 mmol) in tetrahydrofuran (500 mL) at 0° C. was added borane dimethyl sulfide complex (170 mL, 170 mmol). The resulting mixture was stirred with gradual warming to ambient temperature over 15 h, re-cooled to 0° C., and quenched with methanol. The mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, filtered and evaporated in vacuo to yield the title compound as a white solid, which was used without further purification.

Fuente