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

To a solution 5-bromo-2-chlorobenzoic acid (100 g, 425 mmol) in tetrahydrofuran (500 mL) at 0 r 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 MeOH. The mixture was diluted with water and extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous MgSO4, filtered and evaporated in vacuo to yield the titiled compound as a white solid, which was used without further purification.

1. temperaturere-cooled to 0° C.
2. customquenched with MeOH
3. additionThe mixture was diluted with water
4. extractionextracted with EtOAc
5. washThe organic layer was washed with brine
6. dry with materialdried over anhydrous MgSO4
7. filtrationfiltered
8. customevaporated in vacuo

ORD record

ord-069067a6ec314c6db505e56334f948c3

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08586550B2