4-Iodophenol → 1-(3-Chloropropoxy)-4-iodobenzene

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-iodophenol (250 g), potassium carbonate (313.6 g) and 2-butanone (1500 ml) is stirred for 15-20 min. 1-bromochloropropane (357.71 g) is added over about 10 minutes at 25-30° C. After stirring for a further 10 min, the reaction mass is heated to reflux (about 80-85° C.) for 22-24 h. After cooling to 25-30° C., the mixture is filtered, washing the cake with 2-butanone (750 ml). The filtrate is concentrated under reduced pressure at 50-60° C. Ethyl acetate (3750 ml) is added and stirred for 10-20 min to get a clear solution. This is washed with 2N sodium hydroxide solution (1250 ml), water (2500 ml) and aqueous sodium chloride (2500 ml) and then dried with sodium sulfate. The solvent is concentrated under reduced pressure at 50-60° C. n-heptane (250 ml) is added and stirred for about 20 min at 25-30° C. The solution is then cooled to −5 to −10° C. and stirred for about 30 min. The solid is filtered, washed with chilled n-heptane (125 ml, 0-5° C.) and the solid is allowed to dry.

Provenance & Evidence