3-Bromo-2-fluorobenzoic acid → 3-Bromo-2-fluorobenzyl Alcohol

A cooled (0° C.) solution of 3-bromo-2-fluorobenzoic acid (Fluorochem; 500 mg; 2.28 mmol) in anhydrous THF (4 mL) was slowly treated with borane-tetrahydrofuran complex (3.42 mL; 1.00 M; 3.42 mmol) and the resulting solution was stirred at RT for 2 days. Borane-tetrahydrofuran complex (3.42 mL; 1.00 M; 3.42 mmol) was added and the reaction mixture was stirred at RT for a further 3 hours. The reaction was carefully quenched with water and the mixture was concentrated. The residue was dissolved in Et2O, and the aqueous phase was saturated with K2CO3. The organic layer was separated and the aqueous phase was extracted with Et2O. The combined organic phases were washed with water and brine, dried over MgSO4 and concentrated to dryness affording the title compound as a colorless oil.

1. additionwas slowly treated with borane-tetrahydrofuran complex (3.42 mL; 1.00 M; 3.42 mmol)
2. additionBorane-tetrahydrofuran complex (3.42 mL; 1.00 M; 3.42 mmol) was added
3. stirringthe reaction mixture was stirred at RT for a further 3 hours
4. customThe reaction was carefully quenched with water
5. concentrationthe mixture was concentrated
6. dissolutionThe residue was dissolved in Et2O
7. customThe organic layer was separated
8. extractionthe aqueous phase was extracted with Et2O
9. washThe combined organic phases were washed with water and brine
10. dry with materialdried over MgSO4
11. concentrationconcentrated to dryness

ORD record

ord-d117f10c47314581ad4f5f7f25f204d6

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08273769B2