1,4-Dibromobutane → 1-(4-Chlorophenyl)cyclopentanecarbonitrile

To a suspension of sodium hydride (60% suspension in mineral oil) (14.5 g, 362.96 mmol) in dimethyl sulfoxide (250 mL) was added dropwise a mixture of (4-chlorophenyl)acetonitrile (316) (25 g, 164.98 mmol) and 1,4-dibromobutane (35.6 g, 164.98 mmol) dissolved in dimethyl sulfoxide:ether (1:1; 300 mL) at 0° C. The reaction mixture was stirred for 30 min at same temperature and at room temperature for 3 h. After completion of the reaction, the reaction mixture was quenched with HCl (1N; 25 mL) and water (200 mL) and extracted with ethyl acetate (3×100 mL). The separated organic part was washed with water (3×100 mL) and brine (100 mL) and dried and concentrated to get a crude product which was purified by silica CombiFlash column (3-5% ethyl acetate in hexane used as eluent) to afford 1-(4-chlorophenyl)-cyclopentanecarbonitrile (317) (33.9 g, 100%) as a light yellow oil.

1. additionwas added dropwise
2. customAfter completion of the reaction
3. customthe reaction mixture was quenched with HCl (1N; 25 mL) and water (200 mL)
4. extractionextracted with ethyl acetate (3×100 mL)
5. washThe separated organic part was washed with water (3×100 mL) and brine (100 mL)
6. customdried
7. concentrationconcentrated
8. customto get a crude product which
9. customwas purified by silica CombiFlash column (3-5% ethyl acetate in hexane used as eluent)

ORD record

ord-a767d48985b24769ba4cee6a295001c4

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09045486B2