Potassium Carbonate → 4-iodo-1-(3-methyl-4-nitrobenzyl)-2-trifluoroacetyl-1H-pyrrole

HRID 2243261Notes

Reaction equation

HRID 2243261 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH2:5]Cl.[I:13][C:14]1[CH:15]=[C:16]([C:19](=[O:24])[C:20]([F:23])([F:22])[F:21])[NH:17][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[I:13][C:14]1[CH:15]=[C:16]([C:19](=[O:24])[C:20]([F:21])([F:22])[F:23])[N:17]([CH2:5][C:4]2[CH:7]=[CH:8][C:9]([N+:10]([O-:12])=[O:11])=[C:2]([CH3:1])[CH:3]=2)[CH:18]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 87687Alpha-chloro-3-methyl-4-nitrotolueneHCID 592104064-Iodo-2-(trifluoroacetyl)pyrrole

Product 1

HCID 592104184-iodo-1-(3-methyl-4-nitrobenzyl)-2-trifluoroacetyl-1H-pyrroleYield 33.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Methyl-4-nitrobenzyl chloride (0.63 g), 4-iodo-2-(trifluoroacetyl)pyrrole (0.89 g) and potassium carbonate (0.57 g) were stirred in DMF (10 ml) at room temperature for 2 hours. The reaction solution was diluted with ethyl acetate and washed with water and saturated aqueous solution of sodium chloride. After drying the organic layer with magnesium sulfate, the solvent was distilled off under the reduced pressure and the obtained residue was purified by silica gel column chromatography to obtain 4-iodo-1-(3-methyl-4-nitrobenzyl)-2-trifluoroacetyl-1H-pyrrole (0.45 g).

Workup

  1. washwashed with water and saturated aqueous solution of sodium chloride
  2. dry with materialAfter drying the organic layer with magnesium sulfate
  3. distillationthe solvent was distilled off under the reduced pressure
  4. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-70eac498f4c749a4940a15493d4aa70f
Source dataset
uspto-grants-2010_03
Patent number
US07674807B2

Reaction notes

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