Water → HCID 67169043, compound

Participants

Reaction Steps

To a solution of 2-(3,5-dichlorophenyl)acetonitrile (2 g, 10.75 mmol) in N,N-dimethylformamide (40 mL) at 0° C. was added 60% sodium hydride (0.946 g, 23.65 mmol) and the mixture was stirred for 1 min. Then 1,5-dibromopentane (1.464 mL, 10.75 mmol) was added, and the mixture was stirred at 0° C. for 1 hr and at room temperature for 14 hrs. About 100 mL of water was added, and the product was extracted with ethyl acetate. The extract was washed with water and brine. The combined aqueous layers were extracted with ethyl acetate once and washed with brine. The extracts were dried over sodium sulfate and evaporated to give an oily residue. It was purified by Combiflash (120 g silica gel) by eluting with 5:95 EtOAc-hexane to give the desired 1-(3,5-dichlorophenyl)cyclohexanecarbonitrile (2.16 g, 79% yield) as a crystalline solid. 1H NMR (400 MHz, CDCl3) δ ppm 7.38 (2H, d, J=1.76 Hz), 7.32 (1H, t, J=1.76 Hz), 2.14 (2H, d, J=11.86 Hz), 1.67-1.94 (8H, m).

Provenance & Evidence