1,2-Dibromoethane → 2-n-Butyl-3-[4-(2-bromo-ethoxy)-benzoyl]-benzofuran

Participants

Reaction Conditions

Reaction Steps

A mixture of 93.5 g (0.25 mole) of 2-n-Butyl-3-(4-hydroxy-benzoyl)-benzofuran, 69 g (0.5 mole) of finely ground anhydrous potassium carbonate and 500 ml of methyl ethyl ketone was stirred and refluxed for 30 minutes. The mixture was allowed to cool to about 50° C. and 187.8 g (1 mole) of 1,2-dibromo-ethane were added in one operation. Stirring and refluxing were continued for 18 h and a further increment of 47 g of 1,2-dibromo-ethane was added. Refluxing was continued for 6 h, the course of the reaction being monitored by thin-layer chromatography (TLC). Filtration and evaporation to dryness under reduced pressure then followed. The residue was taken up in diethyl ether after which the ethereal solution was washed, first with water, then with a 10% aqueous solution of sodium hydroxide and once again with water. Drying was carried out over sodium sulphate, followed by evaporation to dryness under reduced pressure. In this way 56.5 g of 2-n-butyl-3-[ 4-(2-bromo-ethoxy)-benzoyl]-benzofuran in the form of an oil were obtained.

Provenance & Evidence