Methanol → (2-Bromo-5-fluorophenyl)methanamine

Participants

Reaction Steps

To a solution of 2-bromo-5-fluorobenzonitrile (3.0 g, 15.00 mmol) and NaBH4 (1.419 g, 37.5 mmol) in THF (30 mL) was slowly added TFA (3.47 mL, 45.0 mmol) over a period of 20 min. The resulting mixture was stirred at rt for 16 hours, then MeOH (10 mL) was added and the mixture was stirred for another 30 min. It was then diluted with EtOAc (200 mL), washed with water, dried over Na2SO4 and evaporated. The residue was purified on an 80 g Thompson silica cartridge (3% to 100% B in Hexanes, 1200 mL, B: 10% MeOH in EtOAc). The desired product was obtained as a colorless oil (1.70 g, 8.33 mmol, 55.5% yield). LC/MS (0.647 min, MH+: 205.92). 1H NMR (500 MHz, DMSO-d6) δ ppm 7.59 (1H, dd, J=8.85, 5.49 Hz), 7.43 (1H, dd, J=10.07, 3.05 Hz), 7.05 (1H, td, J=8.47, 3.20 Hz), 3.72 (3H, s), 2.00 (2H, br. s.).

Provenance & Evidence