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

HRID 28660

Reaction equation

HRID 28660 reaction equation
N(OC(C)(C)C)=O.[Br:8][C:9]1[CH:14]=[CH:13][C:12](N)=[C:11]([I:16])[CH:10]=1.[ClH:17]>C(#N)C.[Cu](Cl)Cl>[Br:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:17])=[C:11]([I:16])[CH:10]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10906Tert-Butyl nitriteHCID 8239344-Bromo-2-iodoaniline

Product 1

HCID 510000714-Bromo-1-chloro-2-iodobenzeneYield 76%

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 6342AcetonitrileSolvent2×

Conditions

Temperature
60 °C

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).

Workup

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

Sources & evidence

ORD record
ord-56d0793c4c3147fab76e56c4397753b3
Source dataset
uspto-grants-2008_09
Patent number
US07419984B2

Linked notes

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