1-(3-Bromo-4-fluorophenyl)ethan-1-one → 1-(3-Bromo-4-fluorophenyl)ethanol

Temperature

70 °C

To a solution of 3-bromo-4-fluoroacetophenone (10 g, 46 mmol) in THF (100 mL) and methanol (1.0 mL) was added sodium borohydride (2.1 g, 55.5 mmol). The mixture was heated up to 70° C. for 1 h, then cooled down to rt. The reaction was quenched by 100 ml of 1N HCl solution and extracted with EtOAc (3×100 mL). The combined organic layers were washed with brine, dried over MgSO4, and concentrated. The crude product was purified by column chromatography to give 9.8 g of 84A (97% yield). 1H NMR (400 MHz, CDCl3) δ ppm 1.48 (d, J=6.15 Hz, 3H) 7.24-7.33 (m, 1H) 7.59 (dd, J=6.59, 2.20 Hz, 1H).

1. temperaturecooled down to rt
2. customThe reaction was quenched by 100 ml of 1N HCl solution
3. extractionextracted with EtOAc (3×100 mL)
4. washThe combined organic layers were washed with brine
5. dry with materialdried over MgSO4
6. concentrationconcentrated
7. customThe crude product was purified by column chromatography

ORD record

ord-c14e8ac97c774ed2a5e868ca22b06d13

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07622585B2