Water → 1-(Chloromethyl)cyclopentane-1-carbonitrile

A solution of cyclopentanecarbonitrile (14.3 g, 150 mmol) in THF (25 ml) was added dropwise to a stirred solution of lithium diisopropylamide (158 mmol) in THF (150 ml) and hexane (100 ml), under dry nitrogen, keeping the temperature below -65°. After 0.5 h, the solution was warmed to ambient temperature and added to a stirred solution of bromochloromethane (49.4 ml, 750 mmol) in THF (50 ml) keeping the temperature below -65°. The solution was allowed to warm to ambient temperature and, after 18 h, poured into water (500 ml). The aqueous mixture was extracted with CHCl3 (3×250 ml). The extracts were washed with 2N HCl (100 ml) and H2O (100 ml), dried (MgSO4), and evaporated under reduced pressure to give an oil which was distilled to give a pale yellow oil (8.9 g) b.p. 96° at 10 mmHg.

1. customthe temperature below -65°
2. customthe temperature below -65°
3. temperatureto warm to ambient temperature and, after 18 h
4. extractionThe aqueous mixture was extracted with CHCl3 (3×250 ml)
5. washThe extracts were washed with 2N HCl (100 ml) and H2O (100 ml)
6. dry with materialdried (MgSO4)
7. customevaporated under reduced pressure
8. customto give an oil which
9. distillationwas distilled

ORD record

ord-4492aeacfc8346c79c1d054dfb4a6bff

Source dataset

uspto-grants-1988_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04760158