Ethyl Acetate → [1-(2,5-Dichlorophenyl)-cyclopentyl]-acetonitrile

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of methanesulfonic acid 1-(2,5-dichlorophenyl)-cyclopentylmethyl ester (201) (24 g, 74.53 mmol) in dimethyl sulfoxide (200 mL) KI (1.237 g, 7.453 mmol) and NaCN (5.478 g, 111.801 mmol) were added. The mixture was heated to 140° C. and stirred for 5 h. Silica TLC was performed (10% ethyl acetate in hexane, Rf=0.6). The reaction mixture was cooled to room temperature, diluted with water, extracted with ethyl acetate, washed with brine, dried, concentrated. The obtained crude product was purified using normal silica gel (100-200 mesh) column chromatography using a gradient eluent of 2 to 10% ethyl acetate in hexane to get pure [1-(2,5-dichlorophenyl)-cyclopentyl]-acetonitrile (202) (10.5 g, 55.43%) as a white solid.

Provenance & Evidence