1,5-Dibromopentane → 1-(3,4-Difluorophenyl)cyclohexanecarbonitrile

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Reaction Steps

To a solution of 2-(3,4-difluorophenyl)acetonitrile (2 g, 13.06 mmol) in 20 mL of DMF at 0° C. was added 60% sodium hydride (1.149 g, 28 7 mmol), and the mixture was stirred at the same temperature for 5 mins. Then a solution of 1,5-dibromopentane (1.779 mL, 13.06 mmol) in 20 mL of DMF was added dropwise and the mixture was stirred at a temperature in the range of 0° C. to room temperature for 5 hrs. The reaction was quenched with water, and extracted with EtOAc. The mixture was washed with water and brine. The combined aqueous layers were back extracted with EtOAc once and washed with brine. The combined extracts were dried over Na2SO4 and evaporated to give an oily residue. It was purified by Combiflash (120 g silica gel) eluting with 1:9 EtOAc-hexane to give 1-(3,4-difluorophenyl)cyclohexanecarbonitrile (Int. 3-A, 2.52 g, 11.39 mmol, 87% yield). 1H NMR (400 MHz, CDCl3) δ ppm 7.12-7.35 (3 H, m), 2.14 (2 H, d, J=11.86 Hz), 1.75-1.95 (6 H, m), 1.64-1.75 (2 H, m).

Provenance & Evidence