1,2-Dibromoethane → 5-(2-Bromoethoxy)benzofurazan

Participants

Reaction Steps

Sodium hydroxide (40 mg. 1 mmol) was added to a solution of 5-hydroxybenzofurazan (136 mg, 1 mmol) in ethanol (2 ml) and the mixture was stirred at room temperature for 30 minutes, 1,2-dibromoethane (0.26 ml, 0.56 g, 3 mmol) was added and the mixture was heated under reflux for 20 hours, cooled and the solvent was evaporated under reduced pressure. Aqueous sodium bicarbonate (saturated, 10 ml) was added and the mixture was extracted with dichloromethane (3×10 ml). The combined organic fractions were dried (Na2SO4) and evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with hexane/10% ethyl acetate to give the benzofurazan as a pale yellow oil (99 mg. 41%).

Provenance & Evidence