GENERAL METHOD: Methyl 3-iodo-4-methylbenzoate (10.0 mmol), zinc cyanide (10.0 mmol) and tetrakis(triphenylphosphine)palladium (2.0 mmol) were dissolved in 20 mL of N,N-dimethylformamide (DMF). The reaction mixture was heated and stirred at 80 °C for 5 h under nitrogen protection. After completion of the reaction, the mixture was extracted with dichloromethane (25 mL × 3), the organic layers were combined, washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure to obtain the crude product. Finally, the crude product was purified by silica gel column chromatography to obtain the target compound methyl 3-cyano-4-methylbenzoate.
