1,3-Dibromopropane → HCID 12803794, compound

Participants

Reaction Steps

A methanolic solution of sodium methoxide prepared by dissolving sodium (35.7 g) in anhydrous methanol (300 ml) was treated with 4-(4-chlorophenyl)phenol (311 g) and the resulting solution was added to a stirred solution of 1,3-dibromopropane (850 ml) in anhydrous methanol (500 ml) at reflux during a period of 6 hours. The mixture was stirred at reflux for a further period of 18 hours and was then evaporated to dryness in vacuo. The crystalline residue was triturated with petroleum ether (b.p. 40°-60° C.), filtered off and dried, and was then triturated with aqueous potassium hydroxide solution (1500 ml; 5% w/v), filtered off, washed well with water and dried. The solid was subjected to fractional crystallisation from a mixture of isopropanol and acetone. The first crop was discarded. The second crop (161 g) was dissolved in acetone, filtered, and evaporated. The third crop (53 g) was recrystallised from ethanol. The fourth crop was recrystallised from isopropanol and then twice from ethanol. The purified second, third and fourth crops were combined and dissolved in acetone, and the solution was filtered through diatomaceous earth. It was concentrated in vacuo to a volume of 300 ml and was then diluted with a mixture of methanol (200 ml) and water (500 ml). The resulting solid was filtered off and washed with water to give 3-[4-(4-chlorophenyl)phenoxy]propyl bromide (194 g), m.p. 103°-105° C.

Provenance & Evidence