4-Iodobenzonitrile → 4-Allyl-benzonitrile

Participants

Reaction Steps

Add allyl tri-n-butylstannane (39.3 mmol, 12.18 ml) dropwise to a stirred solution of 4-iodo-benzonitrile (6 g, 26.2 mmol), tetrakis(triphenylphosphine)palladium(0) (1.31 g, 1.5 mmol) and copper (I) iodide (399 mg, 2.09 mmol) in 30 ml of dry 1,4-dioxane under argon atmosphere. Reflux the mixture for 24 hours and then cool to room temperature. Dilute with 40 ml of diethyl ether and add 20 ml of saturated solution of KF and stir for 2 hours. Filter the mixture and wash the organic layer with water (20 ml), brine (20 ml) and dry over sodium sulfate. Evaporate in vacuo and purify by flash chromatography in silica using hexane-ethyl acetate as eluent (20:1) to afford 2.66 g (70%) of 4-allylbenzonitrile

Provenance & Evidence