Triethylamine → 2-Bromo-6-(prop-1-en-2-yl)pyridine

Participants

Reaction Steps

A solution of 2-(6-bromopyridin-2-yl)propan-2-ol (2.44 g, 11.29 mmol) and methansulfonic anhydride (5.90 g, 33.9 mmol) in dichloromethane (35 mL) was charged with triethylamine (6.26 ml, 45.2 mmol). After three hours, the reaction mixture was partitioned between ethyl acetate (50 mL) and saturated aqueous sodium bicarbonate (25 mL). The layers were separated and the organic layer was washed with saturated aqueous sodium bicarbonate (25 mL) and brine (2×25 mL), dried over sodium sulfate, filtered, and concentrated. The resulting yellow liquid was purified by silica gel chromatography (2-20% ethyl acetate/hexanes) to afford the title compound. 1H NMR (600 MHz, d6-DMSO): δ 7.70 (t, 1H), 7.61 (d, 1H), 7.49 (d, 1H), 5.89 (s, 1H), 5.33 (s, 1H), 2.06 (s, 3H).

Provenance & Evidence