4-Fluoro-3-nitrobenzoic acid → 4-Fluoro-3-nitrobenzyl alcohol

Temperature

0 °C

4-Fluoro-3-nitro-benzoic acid (185 mg, 1 mmol) was dissolved in THF (2 ml) and cooled to 0° C. under a nitrogen atmosphere. A Borane/THF solution (2 ml of a 1M solution, 2 mmol) was added dropwise, and the reaction mixture was heated to reflux for 1 h. The reaction was judged complete and quenched with 3N HCl (0.5 ml) and the solvent was removed under vacuum. The reaction mixture was partitioned between ethyl acetate and a sodium carbonate solution. The organic layer was washed with carbonate two additional times, and then it was washed with brine. It was dried over MgSO4, and the solvent was removed to yield the title product (160 mg (95%), 0.94 mmol). 1H NMR (DMSO-d6): δ=8.10 (s, 1H), 7.62 (d, J=7.3 Hz, 1H), 7.32 (d, J=7.3 Hz, 1H), 4.82 (d, J=4.5 Hz, 2H).

1. temperaturethe reaction mixture was heated
2. temperatureto reflux for 1 h
3. customquenched with 3N HCl (0.5 ml)
4. customthe solvent was removed under vacuum
5. customThe reaction mixture was partitioned between ethyl acetate
6. washThe organic layer was washed with carbonate two additional times
7. washit was washed with brine
8. dry with materialIt was dried over MgSO4
9. customthe solvent was removed

ORD record

ord-e4b56798bafa4faa985207a78d440d2b

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07696210B2