Synthesis
Under nitrogen protection, 1500 mL of anhydrous dimethylformamide (DMF) was added to a 1000 mL four-necked flask, followed by 72.67 g (0.6 mol) of p-fluorobenzonitrile and 61.2 g (0.9 mol) of imidazole sequentially. Finally, 21.6 g (0.9 mol) of sodium hydride was slowly added. The reaction mixture was heated to 100 °C, kept at this temperature and stirred for 4 hours, followed by continued stirring at room temperature overnight. Upon completion of the reaction, the mixture was poured into water and extracted with dichloromethane several times. The organic phases were combined, dried over anhydrous sodium sulfate and concentrated on a rotary evaporator. Finally, the product was dried under reduced pressure at 60 °C to give 94 g of 4-(imidazol-1-yl)benzonitrile in 93% yield of the theoretical value. The product was characterized by 1H-NMR (400 MHz, CDCl3): δ= 7.27 (s, 1H); 7.35 (s, 1H); 7.54 (d, J = 8.8 Hz, 2H); 7.81 (d, J = 8.8 Hz, 2H); 7.95 (s, 1H).
References
[1] Synthetic Communications, 2008, vol. 38, # 4, p. 626 - 636
[2] Patent: WO2006/56418, 2006, A2. Location in patent: Page/Page column 57
[3] Patent: US2009/18330, 2009, A1. Location in patent: Page/Page column 14
[4] Advanced Synthesis and Catalysis, 2007, vol. 349, # 11-12, p. 1938 - 1942
[5] Monatshefte fur Chemie, 2004, vol. 135, # 4, p. 419 - 423
