Hydrochloric Acid → 4-Bromo-1-chloro-2-iodobenzene

Participants

Reaction Conditions

Reaction Steps

tert-Butyl nitrite (11.1 ml, 93.3 mmol) is added to a suspension of copper(II) chloride (10.04 g, 75 mmol) in acetonitrile (224 ml) and the mixture is heated with stirring to 60° C. A solution of 4-bromo-2-iodoaniline (18.54 g, 62 mmol) in acetonitrile (56 ml) is added dropwise over about an hour, and once the addition is complete the mixture is stirred at 60° C. for 2 hours. The mixture is cooled to room temperature, poured into 20% aqueous hydrochloric acid (1.3 liters) and extracted with diethyl ether (1.5 liters). The organic extract is separated and the aqueous re-extracted with ether (1 liter). The organic extracts are combined and dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated in vacuo. The residue is further purified by column chromatography on silica gel to give 4-bromo-1-chloro-2-iodobenzene (8.62 g) as an oil.

Provenance & Evidence