Pyrazole → 4-(1-Pyrazolyl)benzonitrile

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-fluorobenzonitrile (1.5 g, 12.35 mmol) and pyrazole (0.843 g, 12.38 mmol) in DMF (10 mL) was added NaH (60% in oil, 0.644 g, 16.09 mmol). The reaction was heated to 145° C. for 20 h. The reaction was cooled to room temperature and was diluted with water and EtOAc The aqueous layer was washed with EtOAc (3×) and the combined organic layers were washed with water (4×). The organic solution was dried (MgSO4, filtered, and concentrated. Medium pressure chromatography (4:1 hexanes:EtOAc) provided 4-pyrazol-1-yl-benzonitrile (1.6 g) as a white solid. 1H NMR (400 MHz, CDCl3) δ 7.97 (d, 1H), 7.82 (d, 2H), 7.73 (m, 3H), 6.87 (d, 1H); MS 170 (M+1).

Provenance & Evidence