Diethyl Ether → 1-(3,4-Dichlorophenyl)cyclopentanecarbonitrile

Participants

Reaction Steps

1,4-Dibromobutane (106 ml) was added dropwise over 1 hour at 70°-80° C. under nitrogen to a stirred mixture of 3,4-dichlorophenylacetonitrile (150 g) , benzyltriethylammonium chloride (2 g) and 50% aqueous sodium hydroxide solution (300 ml). When the addition was complete the mixture was stirred at 70°-80° C. for 2 hours, then cooled to ambient temperature. Ether (400 ml) and water (200 ml) were added and the layers were separated. The aqueous layer was washed with ether (2×200 ml), then the combined organic solutions were dried over magnesium sulphate and the solvent removed in vacuo. The residue was distilled to give 1-(3,4-dichlorophenyl)cyclopentanecarbonitrile as a pale yellow oil (135 g), b.p. 132°-140° C./0.4 mbar.

Provenance & Evidence