Iodine → 4-Iodo-2-(trifluoroacetyl)pyrrole

HRID 2243260Notes

Reaction equation

HRID 2243260 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]([C:5]1[NH:6][CH:7]=[CH:8][CH:9]=1)=[O:4].[N+]([O-])([O-])=O.[NH4+].[Ce].[Ce].[I:19]I>C(#N)C>[I:19][C:8]1[CH:9]=[C:5]([C:3](=[O:4])[C:2]([F:1])([F:10])[F:11])[NH:6][CH:7]=1

Participants

5

Reactant 3

HCID 807IodineHCID 137637Ethanone, 2,2,2-trifluoro-1-(1H-pyrrol-2-yl)-HCID 86617141Dicerium ammonium nitrate

Product 1

HCID 592104064-Iodo-2-(trifluoroacetyl)pyrroleYield 112.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

An acetonitrile solution (20 ml) of 2-(trifluoroacetyl)-1H-pyrrole (0.5 g), dicerium ammonium nitrate (0.84 g) and iodine (0.47 g) was refluxed for 2 hours. After cooling, the reaction solution was washed with saturated aqueous solution of sodium thiosulfate and saturated aqueous solution of sodium chloride. After drying the organic layer with magnesium sulfate, the solvent was distilled off under the reduced pressure to obtain 4-iodo-2-(trifluoroacetyl)-1H-pyrrole (0.6 g).

Workup

  1. temperatureAfter cooling
  2. washthe reaction solution was washed with saturated aqueous solution of sodium thiosulfate and saturated aqueous solution of sodium chloride
  3. dry with materialAfter drying the organic layer with magnesium sulfate
  4. distillationthe solvent was distilled off under the reduced pressure

Sources & evidence

ORD record
ord-5a43c9b40c4a49bdb194188d71139fae
Source dataset
uspto-grants-2010_03
Patent number
US07674807B2

Reaction notes

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