Thionyl Chloride → 5-(6-Chlorohexyl)pyrimidine

Participants

Reaction Steps

A solution of 20.6 g of 5-pyrimidinehexanol in 80 ml of dichloromethane was cooled in an ice bath as a solution of 12.3 ml of thionyl chloride in 40 ml of dichloromethane was added dropwise. The mixture was stirred at room temperature for 1 hour and at reflux temperature for 1 hour, was concentrated, azeotroped with toluene, diluted with dichloromethane and washed with water, saturated sodium bicarbonate, and brine. Evaporation gave 22.3 g of 6-(5-pyrimidinyl)hexylchloride.

Provenance & Evidence