Trifluoroacetic acid → HCID 67260294, compound

Participants

Reaction Steps

To a solution of 5-(2,4-difluorobenzyl)pyridin-2(1H)-one 3 (1.89 g, 8.5 mmol) in acetic acid (34 ml) was added TFA (2.2 ml), followed by N-iodosuccinimide (2.02 g, 8.5 mmol). The red homogeneous solution was allowed to stir overnight at room temperature, poured onto ice and neutralized with cone. NH4OH. The solid was collected by filtration, rinsed with water, treated with methanol/dichloromethane, dried over sodium sulfate, and evaporated. The resulting brown solid was purified by flash column chromatography on silica gel (hexanes:ethyl acetate, 50:50). Yield 2.57 g (87%). 1H NMR (CDCl3, 500 MHz): δ 13.20 (s, 1H), 7.98 (d, 1H, J=2.2 Hz), 7.26-6.81 (m, 4H), 3.70 (s, 2H). 13C NMR (CDCl3, 125 MHz): δ 162.5, 161.9, 160.5, 151.9, 133.5, 131.2, 121.8, 120.0, 111.6, 104.3, 91.6, 29.9.

Provenance & Evidence