Isopropanol → 1-(3,4-Dichlorophenyl)-1-cyclobutane-carbonitrile

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Reaction Steps

A solution of 3,4-dichlorobenzyl cyanide (25 g) and 1,3-dibromopropane (15 ml) in dry dimethyl sulfoxide (150 ml) was added dropwise under nitrogen to a stirred mixture of sodium hydride (7.5 g), which was dispersed in mineral oil (7.5 g), and dimethyl sulfoxide (200 ml) at 30-35° C. The mixture was stirred at room temperature for 2 hours, and 2-propanol (8 ml) and then water (110 ml) were added dropwise. The mixture was filtered through diatomaceous earth which is marketed under the proprietary name CELITE, and the solid residue was washed with ether. The ether layer was separated off, washed with water, dried and evaporated. 1-(3,4-dichlorophenyl)-1-cyclobutane-carbonitrile was isolated by distillation (boiling point: 108 to 120° C. under 0.2 mbar. This procedure is a modification of the process described by Butler and Pllatz (J. Org. Chem. 36 No. 9 (1971) 1308).

Provenance & Evidence