Hydrochloric Acid → 2-(2-Bromo-4-fluorophenyl)ethan-1-ol

To a solution of 2-(2-bromo-4-fluorophenyl)acetic acid (2.3 g, 9.87 mmol) in THF (20 mL) at 0° C. was added 1M BH3.THF comples (14.80 mL, 14.80 mmol) in THF and the resulting mixture was stirred at room temp for 3 h. 1N HCl (50 mL) was then added and the mixture was extracted with ethyl acetate (200 mL), washed with brine (50 mL), dried (Na2SO4), filtered and concentrated to afford 2-(2-bromo-4-fluorophenyl)ethanol (2.0 g, 9.13 mmol, 93% yield) as colorless oil. 1H NMR (500 MHz, CDCl3) δ 7.33 (dd, J=8.4, 2.7 Hz, 1H), 7.30-7.24 (m, 1H), 7.01 (td, J=8.2, 2.6 Hz, 1H), 3.89 (q, J=6.6 Hz, 2H), 3.02 (t, J=6.6 Hz, 2H), 1.43 (t, J=5.8 Hz, 1H).

1. extractionthe mixture was extracted with ethyl acetate (200 mL)
2. washwashed with brine (50 mL)
3. dry with materialdried (Na2SO4)
4. filtrationfiltered
5. concentrationconcentrated

ORD record

ord-0dde3b99e43d42b3b59d98421818c9a9

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09273067B2