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

Temperature

0 °C

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.

1. additionis added
2. stirringis vigorously stirred
3. additionAfter addition
4. temperatureto warm to room temperature
5. customthe phases are separated
6. extractionThe aqueous phase is extracted with ethyl acetate (3×)
7. washThe combined organic phases are washed successively with 1N NaOH, 1N sodium thiosulfate, 1N HCl, aq.sat
8. dry with materialsodium bicarbonate solution and brine, then dried over sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure
11. customThe resulting residue is purified by flash chromatography (SiO2 60 F)

ORD record

ord-107c19d325124f7db454654f3e05a514

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08324235B2