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

Temperature

60 °C

tert-Butyl nitrite (3 ml, 25 mmol) is added to a suspension of copper(II) chloride (2.71 g, 20 mmol) in acetonitrile (60 ml) and the mixture is heated with stirring to 60° C. A solution of 4-bromo-2-iodoaniline (5 g, 17 mmol) in acetonitrile (15 ml) is added dropwise, and once the addition is complete the mixture is stirred at 60° C. for 2.5 hours. The mixture is cooled to room temperature, poured into 20% aqueous hydrochloric acid and extracted with diethyl ether. The organic extract is 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 (4.32 g) as an oil.

1. temperaturethe mixture is heated
2. additiononce the addition
3. stirringis stirred at 60° C. for 2.5 hours
4. temperatureThe mixture is cooled to room temperature
5. extractionextracted with diethyl ether
6. extractionThe organic extract
7. dry with materialis dried over anhydrous magnesium sulfate
8. filtrationfiltered
9. customthe filtrate evaporated in vacuo
10. customThe residue is further purified by column chromatography on silica gel

ORD record

ord-8b4ff47eb8f44f658865f33296eccc5a

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08680012B2