Potassium Iodide → 1-Bromo-4-chloro-2-iodobenzene

Participants

Reaction Conditions

Reaction Steps

A suspension of 2-bromo-5-chlorobenzenamine (11.348 g, 54.963 mmol) in concentrated HCl (100 mL) was cooled to 0° C. and treated dropwise (using an addition funnel) over 20 minutes with a solution of sodium nitrite (4.5506 g, 65.955 mmol) in water (20 mL). The reaction was stirred at 0° C. for 75 minutes. A solution of potassium iodide (27.372 g, 164.89 mmol) in water (50 mL) was added, and the reaction was stirred at 23° C. After 1 hour, the reaction was heated to 70° C. After 18 hours, the reaction was diluted with EtOAc (500 mL) and washed with water (300 mL), a 2N NaOH solution (300 mL), saturated sodium thiosulfate solution (300 mL) and brine (250 mL), dried over MgSO4, concentrated in vacuo, and purified by silica gel chromatography (eluant: hexane), affording 11.11 g of 1-bromo-4-chloro-2-iodobenzene.

Provenance & Evidence