Acetyl chloride → HCID 66735718, compound

Participants

Reaction Steps

To a solution of 2-bromo-picolinonitrile (25.8 g, 141.0 mmol) in THF (500 ml) was added a solution of MeMgBr (120.8 ml, 169.2 mmol) in THF at 0° C. The reaction was stirred at room temperature for 1.5 hours, followed by dropwise addition of acetyl chloride (15 ml, 211.5 mmol). The reaction mixture was stirred at room temperature for 16 hours. Saturated sodium bicarbonate solution (50 ml) was added and extracted with EtOAc (2×200 ml). The combined organic was dried over sodium sulfate. After removal of solvent, the resulted residue was purified by column chromatography (hexane-EtOAc=2.5:1) to give the title compound as a white solid (7.5 g, 22%). 1H NMR (400 MHz) δ 9.41 (s, 1H), 8.70 (d, J=2.4 Hz, 1H), 8.10 (dd, J=2.4 and 8.4 Hz, 1H), 7.73 (d, J=8.8 Hz, 1H), 6.02 (s, 1H), 5.59 (s, 1H), 2.07 (s, 3H). MS: Calcd.: 240. Found: [M+H]+ 241.

Provenance & Evidence