Dimethylformamide → HCID 22996227, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-bromo-4-methoxy-2-propoxy-benzene (500 mg, 2.04 mmol) in dimethylformamide (10 mL) at room temperature was added zinc cyanide (240 mg, 2.04 mmol). The reaction mixture was degassed by passing argon through for 2 h before tetrakis(triphenylphosphine)palladium (236 mg, 0.204 mmol) was added. The reaction mixture was heated at 90-100° C. under argon for 12 h. The reaction mixture was taken up in diethyl ether (10 mL) and sodium bicarbonate solution (2 mL). The product was extracted with diethyl ether (2×20 mL). The organic layers were washed with water (1×5 mL), brine (1×5 mL), and dried over anhydrous sodium sulfate. The solid was then filtered off, and the filtrate was concentrated in vacuo. Purification of the crude residue by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel) eluting with 15-20% ethyl acetate in hexanes yielded 4-methoxy-2-propoxy-benzonitrile (290 mg, 74%) as white solids.

Provenance & Evidence