Methyl iodide → (4-Bromophenyl)(butyl)sulfane

Participants

Reaction Steps

4-Bromobenzenethiol (5 g, 26.44 mmol) was added to a solution of sodium methoxide (1.43 g, 26.48 mmol) in 20 ml of anhydrous methanol. The mixture was stirred for 30 min under nitrogen at room temperature and a solution of methyl iodide (4.51 g, 31.77 mmol) in 20 ml anhydrous methanol was then added. The reaction mixture was stirred overnight at room temperature, poured into 2 M of NaOH aqueous solution (30 ml) and extracted three times with ether (3×100 ml ). The combined organic layer was washed with saturated sodium chloride solution and dried over anhydrous magnesium sulfate. After removal of solvent, the product was purified by distillation at 117-119° C. (0.5 mmHg) and was isolated in 88.4% (5.72 g) yield.

Provenance & Evidence