Hydrochloric Acid → (2-Chloro-3-fluorophenyl)methanamine

Participants

Reaction Conditions

Reaction Steps

BH3.THF in THF (1.0 M, 50.0 ml) was carefully added into the THF (40.0 ml) solution of 2-chloro-3-fluorobenzonitrile (662 mg, 4.17 mmol) at rt. The resulting mixture was heated at 70° C. under an atmosphere of nitrogen for 16 h. After cooling to ambient temperature, conc. HCl (5.18 ml, 62.5 mmol) was added slowly. The combined mixture was heated at 70° C. for 30 min. After that time, the mixture was concentrated in vacuo to remove most of solvent, water (20 ml) was added, and the mixture was extracted with Et2O (3×30 ml). The extracts were washed with water (20 ml). The combined aqueous layers were basified by saturated Na2CO3 until pH=9 and extracted with EtOAc (3×50 ml). These EtOAc extracts were washed with brine (50 ml) dried over MgSO4, filtered, and concentrated in vacuo to give the title compound as colorless oil. 1H NMR (400 MHz, CDCl3): δ=1.67 (brs, 2H), 3.97 (s, 2H), 7.03-7.09 (m, 1H), 7.17-7.26 (m, 2H). MS(ES+): m/z=160.14/162.09 (64/32) [MH+]. HPLC: tR=0.40 & 0.70 min (polar—5 min, ZQ3; peak splitting).

Provenance & Evidence