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 then treated in a dropwise fashion over 20 minutes using an addition funnel 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), 2N NaOH solution (300 mL), saturated sodium thiosulfate solution (300 mL), and brine (250 mL). The organic layer was 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