Water → 4-Ethyl-2-isopropoxy-benzonitrile

Participants

Reaction Conditions

Reaction Steps

4-Ethyl-1-iodo-2-isopropoxy-benzene (0.93 g, 3.2 mmol) was dissolved in dimethylformamide (5 mL). Zinc cyanide (226 mg, 1.92 mmol) was added. Argon gas was passed through the mixture for 10 min. Tetrakis(triphenylphosphine)-palladium(184 mg, 0.16 mmol) was added and the mixture was heated at 90° C. for 5 h. The reaction mixture was cooled to room temperature and poured into water. The mixture was extracted with diethyl ether. The organic extracts were washed with brine and dried over anhydrous magnesium sulfate. The solid was then filtered off, and the filtrate was concentrated in vacuo. Purification of the residue by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel) eluting with 10% diethyl ether in hexanes yielded 4-ethyl-2-isopropoxy-benzonitrile (0.34 g, 56%).

Provenance & Evidence