Dimethyl Sulfoxide → 1-(3-Chlorophenyl)cyclobutane-1-carbonitrile

Participants

Reaction Steps

According to the procedure of Butler and Pollatz (Butler, D. E. and J. C. Pollatz, J. Org. Chem. 36:1308 (1971), a reaction flask fitted with a mechanical stirrer, pressure equalizing addition funnel and thermometer was charged, under nitrogen, with 162 ml of DMSO; 17.62 g (0.44 mol) of 60% Nail/oil dispersion was added in portions over 5 minutes. A 20° C. water bath was applied while a solution of 24.5 g (0.162 mol) of (3-chlorophenyl)acetonitrile and 35.9 g (0.195 mol) of 1,3-dibromopropane in Et2O (100 ml) was added during 75 minutes with good stirring at such a rate that the reaction temperature was kept below 33° C. The mixture was stirred at 20° C. for 2 hours when it was cooled in an ice bath and treated cautiously with 8 ml of 2-propanol. The mixture was stirred at 10° C. for 15 minutes when it was treated cautiously with 120 ml of H20 at such a rate that the reaction temperature was kept below 15° C. After 15 minutes, the layers were separated and the aqueous layer was extracted with 4 portions of Et2O. The extracts were combined with the organic layer and this mixture was dried (MgSO4) and concentrated. A red oil was separated from the mineral oil and distilled to give 15.8 g (51%) of the titled product, b.p. 106°-110° C. (0.9 mm Hg).

Provenance & Evidence