Dimethylformamide → 2-[2-(4-Fluorophenyl)-2-oxoethyl]cycloheptan-1-one

Participants

Reaction Steps

A solution of 32,6 g (0.15 mole) of p-fluorophenacylbromide in 100 ml. of dry dimethylformamide is added dropwise to a cooled solution of 25 g (0.15 mole) of 1-pyrrolidino-1-cycloheptene in 100 ml. of dry dimethylformamide. After stirring at ambient temperature for 20 hours, and at 100° C. for 5 hours, 250 ml. of water are added, and the mixture is stirred for 3 hours. The reaction mixture is poured into 1500 ml. of water, extracted with chloroform, and the chloroform extract is washed with water and dried. Removal of the chloroform leaves 2-(p-fluorophenacyl)cycloheptanone as an oil. Infrared and nuclear magnetic resonance spectra confirm the above structure.

Provenance & Evidence