Synthesis
General procedure for the synthesis of 3-ethylbenzonitrile from 3-bromoethylbenzene and zinc cyanide: 1-bromo-3-ethylbenzene (1.1 g), zinc cyanide (508 mg) and tetrakis(triphenylphosphine)palladium (333 mg) were dissolved in anhydrous toluene (8 mL) and degassed. The mixture was transferred to a sealed pressure tube under argon atmosphere and the reaction was stirred at 80°C for 12 hours. After completion of the reaction, the mixture was concentrated to dryness. The remaining residue was purified by column chromatography (silica gel as stationary phase and cyclohexane/ethyl acetate = 95:5 as eluent) to afford the target product 3-ethylbenzonitrile (470 mg, 62% yield). Mass spectrometry analysis showed [MH]+=132.
References
[1] Patent: US2006/173183, 2006, A1. Location in patent: Page/Page column 82
[2] Patent: US2005/272779, 2005, A1. Location in patent: Page/Page column 57
[3] Patent: WO2004/14881, 2004, A2. Location in patent: Page 99
