2-Bromo-4-fluorobenzoic acid → (2-Bromo-4-fluorophenyl)methanol

To a solution of 2-bromo-4-fluorobenzoic acid (20 g; 91 mmol) in anhydrous THF (300 ml) at −10° C. was added dropwise borane tetrahydrofuran complex (1.0M soln in THF) (136.5 ml; 136.5 mmol). After complete addition the reaction was allowed to stir at room temperature for 4 hours. The reaction was quenched by the dropwise addition of water (20 ml). To the mixture was added saturated K2CO3 (200 ml) and water (300 ml). The organic layer was separated and the aqueous extracted with Et2O (2×300 ml). The combined organics were washed with water (2×500 ml), saturated NaCl (200 ml), dried over Na2SO4, filtered and evaporated to give the title compound (18 g, 96%) as a white solid.

1. additionAfter complete addition the reaction
2. customThe reaction was quenched by the dropwise addition of water (20 ml)
3. additionTo the mixture was added saturated K2CO3 (200 ml) and water (300 ml)
4. customThe organic layer was separated
5. extractionthe aqueous extracted with Et2O (2×300 ml)
6. washThe combined organics were washed with water (2×500 ml), saturated NaCl (200 ml)
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. customevaporated

ORD record

ord-af573077381148e0a10e7bd0dfd66a26

Source dataset

uspto-grants-2007_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07285563B2