反应详情

Ammonium chloride (24.2 mg, 0.453 mmol) was added to a mixture of (1S)-2,2-difluoro-1-(3′-fluoro-5′-nitrobiphenyl-4-yl)ethanol (269 mg, 0.905 mmol) and iron (253 mg, 4.53 mmol) in ethanol (6 mL) and water (3 mL). The mixture was heated to reflux for 1.5 hours. Upon cooling to room temperature, the reaction mixture was filtered through CELITE and washed with ethyl acetate. The filtrate was washed with saturated aqueous NaHCO3 and brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (ethyl acetate/hexanes) to yield (1S)-1-(3′-amino-5′-fluorobiphenyl-4-yl)-2,2-difluoroethanol. MS ESI calc'd. for C14H13F3NO [M+H]+ 268, found 268.

1. temperatureThe mixture was heated
2. temperatureto reflux for 1.5 hours
3. filtrationthe reaction mixture was filtered through CELITE
4. washwashed with ethyl acetate
5. washThe filtrate was washed with saturated aqueous NaHCO3 and brine
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customThe residue was purified by silica gel chromatography (ethyl acetate/hexanes)