Zinc cyanide (1.57 g, 13.40 mmol) was added to a solution of 3-tert-butylphenyl trifluoromethanesulfonate (1.5 g, 6.70 mmol) in N,N-dimethylformamide (DMF, 10 mL). The reaction mixture was heated to 120 °C and the reaction was stirred at this temperature for 4 hours. Upon completion of the reaction, the mixture was cooled to room temperature, diluted with ether (2500 mL) and subsequently washed twice with 2N ammonium hydroxide solution (50 mL x 2). The organic phase was separated, washed with saturated sodium chloride solution (20 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography with the eluent being hexane solution of 5% ethyl acetate to give 3-tert-butylbenzonitrile in 75% yield.
