Potassium Iodide → 1-Bromo-5-chloro-4-fluoro-2-iodobenzene

Participants

Reaction Conditions

Reaction Steps

99 mmol of 2-bromo-4-chloro-5-fluoro-phenylamine [120694-11-3] is dissolved in 700 ml of water and 100 ml of concentrated sulfuric acid. The solution is cooled to 0° C. and 109 mmol of sodium nitrite dissolved in 30 ml of water is added. The mixture is stirred for 1 hour at 5-10° C. then a solution of 130 mmol of potassium iodide in 100 ml of water is added slowly whilst the mixture is vigorously stirred. After addition, the mixture is allowed to warm to room temperature. Ethylacetate is added and the phases are separated. The aqueous phase is extracted with ethyl acetate (3×). The combined organic phases are washed successively with 1N NaOH, 1N sodium thiosulfate, 1N HCl, aq.sat. sodium bicarbonate solution and brine, then dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue is purified by flash chromatography (SiO2 60 F) to afford the title compound which is identified based on the Rf value.

Provenance & Evidence