Reaction #56938

Reaction equation

tert-butyl nitrite

4-bromo-2-iodo-phenylamine

hydrochloric acid

→

4-bromo-1-chloro-2-iodo-benzene

Yield 76.0%

Solvents

acetonitrile

acetonitrile

Conditions

Workup

1. 1
   Extractionextracted with ether (2×30 ml)
2. 2
   OtherThe crude product was purified by flash chromatography on silica gel eluting with hexane

Procedure

To a stirred suspension of copper (II) chloride (1.62 g, 12.0 mmol) and tert-butyl nitrite (15.0 mmol) in acetonitrile (40 ml), heated at 60° C., was added a solution of 4-bromo-2-iodo-phenylamine (2.98 g, 10.0 mmol) in acetonitrile (10 ml) dropwise over 50 minutes. After stirring at 60° C. for 1 hour, the mixture was poured into 20% hydrochloric acid (200 ml) and extracted with ether (2×30 ml). The crude product was purified by flash chromatography on silica gel eluting with hexane to provide 4-bromo-1-chloro-2-iodo-benzene (2.4 g, 76% yield).

Source