Water → (4-Bromo-3-fluorophenyl)methanol

4-Bromo-3-fluorobenzoic acid (40.8 g, 0.187 mol) was dissolved in THF (250 ml) with magnetic stirring under Ar in an ice-H2O bath. The cloudy solution was treated dropwise with borane-THF complex (1 M) (374 mL, 0.374 mol) over a 1 h period maintaining the internal temperature at <10° C. The reaction mixture was left to warm to ambient temperature overnight, then cooled in an ice H2O bath and treated dropwise with H2O (150 mL). The THF was removed on a rotary evaporator, and the residue partitioned between EtOAc and H2O. The aqueous layer was extracted with EtOAc (3×100 mL), the organic layers combined, washed with brine, and dried (Na2SO4), filtered, and concentrated to give the title compound as an oil which solidified on standing.

1. additionThe cloudy solution was treated dropwise with borane-THF complex (1 M) (374 mL, 0.374 mol) over a 1 h period
2. temperaturemaintaining the internal temperature at <10° C
3. waitThe reaction mixture was left
4. temperaturecooled in an ice H2O bath
5. customThe THF was removed on a rotary evaporator
6. customthe residue partitioned between EtOAc and H2O
7. extractionThe aqueous layer was extracted with EtOAc (3×100 mL)
8. washwashed with brine
9. dry with materialdried (Na2SO4)
10. filtrationfiltered
11. concentrationconcentrated

ORD record

ord-30e8de07f51c43bd9c7fe4c72705a241

Source dataset

uspto-grants-2001_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06297239B1