Hydrochloric Acid → 2-(4-Fluorophenyl)propan-1-ol

To a solution of 2-(4-fluorophenyl)propanoic acid (1 g, 5.95 mmol) in THF (20 mL) at 0° C. was added 1M BH3.THF (11.89 mL, 11.89 mmol) in THF and the resulting mixture was stirred at room temp for 3 h. Then, 1N HCl (3 mL) was added and the mixture was extracted with ethyl acetate 100 mL), washed with brine (50 mL), dried (Na2SO4), filtered and concentrated. The residue was then purified by Biotage (5-50% EtOAc/hexane) to afford 2-(4-fluorophenyl)propan-1-ol (300 mg, 1.946 mmol, 32.7% yield) as colorless oil. 1H NMR (500 MHz, CDCl3) δ 7.23 (dd, J=8.5, 5.5 Hz, 2H), 7.04 (t, J=8.7 Hz, 2H), 3.79-3.63 (m, 2H), 2.97 (sxt, J=6.9 Hz, 1H), 1.34 (t, J=5.5 Hz, 1H), 1.29 (d, J=7.1 Hz, 3H).

1. extractionthe mixture was extracted with ethyl acetate 100 mL),
2. washwashed with brine (50 mL)
3. dry with materialdried (Na2SO4)
4. filtrationfiltered
5. concentrationconcentrated
6. customThe residue was then purified by Biotage (5-50% EtOAc/hexane)

ORD record

ord-e5f5355da6184de5a95507089e069e74

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09193720B2