Hydrochloric Acid → 4-Amino-3-(bromomethyl)-2-(trifluoromethyl)benzonitrile

Participants

Reaction Steps

To a stirred solution of the diphenylmethylidene from step E (0.250 g, 0.56 mmol) in THF (4 mL) was added 2N HCl (0.4 mL). After stirring at rt for 2 h, the reaction was partitioned in EtOAc/hexanes (20 mL; 1:2). The layers were separated and the organic portion was dried (MgSO4) and concentrated. Purification by SiO2 chromatography (10-50% EtOAc in hexane2) afforded 4-amino-3-(bromomethyl)-2-(trifluoromethyl)benzonitrile (0.073 g, 50%) as a yellow solid: 1H NMR (400 MHz, DMSO-d6) δ 7.61 (d, J=8.6 Hz, 1H), 6.98 (d, J=8.6 Hz, 1H), 6.82 (bs, 2H), 4.71 (s, 2H).

Provenance & Evidence