Bis(2-bromoethyl) ether → HCID 20255643, compound

Participants

Reaction Steps

A mixture of 22.8 g (0.141 mole) of 6-amino-3,5-dimethylbenzofuran, 65.8 g (0.283 mole) of 2,2'-dibromodiethyl ether, 36.1 g (0.279 mole) of N-ethyldiisopropylamine and 210 ml of ethanol is boiled under reflux for 16 hours. The residue obtained after removal of the ethanol in vacuo is taken up in methylene chloride and washed twice with dilute sodium bicarbonate solution. The organic phase is dried, concentrated by evaporation and the crude product is chromatographed over silica gel with petroleum ether/ether. The excess 2,2'-dibromodiethyl ether is removed in a water-jet vacuum over a Vigreux column and the residue is purified by means of solid distillation (110°-115°/4.10-2 torr). 3,5-dimethyl-6-morpholinobenzofuran is obtained having a melting point of 69°-70°.

Provenance & Evidence