Dibromomethane → 1-Bromo-2-(4-chlorophenyl)-2-cyano-4-phenoxybutane

Participants

Reaction Steps

To a flask was added 6.1 g. (0.127 mole) of a 50% oil dispersion of sodium hydride. After washing the sodium hydride several times with hexane to remove the mineral oil, 50 ml. of dry DMF was added, then a solution of 30 g. (0.11 mole) of 2-(4-chlorophenyl)-4-phenoxybutanenitrile in 25 ml. of dry DMF was added dropwise at 0° C. The reaction was stirred and allowed to warm to room temperature over 1.5 hours, then 21.2 g. (0.127 mole) of dibromomethane was added dropwise at 15° C. Upon completion of the addition, the reaction was stirred and heated to 50° C. and was complete in three hours. The reaction mixture was cooled to room temperature, diluted with 300 ml. of water, and then extracted three times with 100 ml. portions of methylene chloride. The combined extracts were washed with dilute hydrochloric acid and water, then dried using sodium sulfate. Upon removal of the solvent, 31 g. of 1-bromo-2-(4-chlorophenyl)-2-cyano-4-phenoxybutane was obtained (77% yield).

Provenance & Evidence