Water → Benzo(b)thiophene, 3-bromo-

Participants

Reaction Steps

A solution of bromine (20.4 ml, 0.40 mole) in chloroform (100 ml) was added dropwise over 1 hour to a stirred mixture of benzothiophene (53.6 g, 0.40 mole) and anhydrous sodium acetate (54.4 g, 0.68 mole) in chloroform (300 ml) at room temperature. The reaction mixture became much thicker during the addition, so a further 300 ml of chloroform was added to aid stirring. After completing the addition, the reaction mixture was stirred for a further 2 hours and then water added (200 ml) to dissolve the inorganic solid. The chloroform layer was separated and washed with water (1×200 ml), sodium hydrogen carbonate solution (1×200 ml) and brine (1×200 ml); then dried (MgSO4) and evaporated to dryness to give a quantitative yield of the title compound as a yellow oil.

Provenance & Evidence