Water → HCID 67169043, compound

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).

1. stirringthe mixture was stirred at 0° C. for 1 hr and at room temperature for 14 hrs
2. extractionthe product was extracted with ethyl acetate
3. washThe extract was washed with water and brine
4. extractionThe combined aqueous layers were extracted with ethyl acetate once
5. washwashed with brine
6. dry with materialThe extracts were dried over sodium sulfate
7. customevaporated
8. customto give an oily residue
9. customIt was purified by Combiflash (120 g silica gel)
10. washby eluting with 5:95 EtOAc-hexane

ORD record

ord-659bc8ddce89447cabcdd756b1d7e1be

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09216972B2