5-Bromo-2-chlorobenzoic acid → (5-Bromo-2-chlorophenyl)methanol

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.

1. temperaturere-cooled to 0° C.
2. customquenched with methanol
3. additionThe mixture was diluted with water
4. extractionextracted with ethyl acetate
5. washThe organic layer was washed with brine
6. dry with materialdried over magnesium sulfate
7. filtrationfiltered
8. customevaporated in vacuo

ORD record

ord-a7d997ae33df466fa0c15625ca28bdcb

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08541380B2