Hydrochloric Acid → HCID 57517571, compound

Participants

Reaction Steps

To a solution of 2-(5-bromopyridin-2-yl)-2-methylpropanenitrile (2.0 g, 8.9 mmol) in dichloromethane (20 mL) under nitrogen was added 1 N solution of DIBAL-H in THF (12.4 mL, 12.4 mmol) dropwise at −30° C. The resulting solution was stirred at ambient temperature for 3 hours before the addition of 2 N hydrochloric acid aqueous solution (10 mL) at 0° C. After stirred at ambient temperature for 10 minutes, the solution was basified with saturated aqueous sodium bicarbonate solution to pH 8-9, and then extracted with ethyl acetate (3×20 mL). All the organic solution was dried over sodium sulfate, filtered and concentrated in vacuo. The crude residue was purified by flash column chromatography with 2-4% ethyl acetate in hexane to afford the title compound as a yellow oil. MS ESI: [M+H]+ m/z 228, 230; 1H NMR (300 MHz, CDCl3) δ 9.73 (s, 1H), 8.66 (s, 1H), 7.82 (d, J=8.7 Hz, 1H), 7.17 (d, J=8.7 Hz, 1H), 1.47 (s, 6H).

Provenance & Evidence