PyBOP → 2-[4-(Trifluoromethoxy)phenyl]acetamide

Participants

Reaction Steps

4-(Trifluoromethoxy)phenylacetic acid (2 g, 9.085 mmol) was dissolved in DMF (20 ml, dry) and PyBOP (4.728 g, 9.085 mmol) was added. The mixture was stirred in an ice-bath and ammonia gas was bubbled in for 5 mins. The ice-bath was removed and the mixture was stirred at rt overnight and then evaporated in vacuum. Water (50 ml) was added into the residue and it was extracted with EtOAc (20 ml×3). The extracts were combined, washed with saturated aqueous NaHCO3 (15 ml), water (20 ml×3), brine (15 ml), dried (MgSO4) and evaporated. The residue was purified by column chromatography (ISOLUTE SI, 20 g/70 ml), eluting with DCM, then MeOH/DCM (1:99), to give the title compound (1.14 g, 57%) as a white solid. Mass Spectrum: M−H+ 218. 1H NMR (400 MHz, CD3OD): δ 3.53 (s, 2H), 7.20 (d, 2H), 7.38 (d, 2H). 13C NMR (100 MHz, CD3OD): 42.5, 121.9 (q, J=253 Hz), 122.1, 131.8, 136.3, 149.4, 176.2.

Provenance & Evidence