Water → 4-[2-(3-bromophenyl)-2-oxo-acetyl]-1H-pyrrole-2-carbonitrile

HRID 2220478Notes

Reaction equation

HRID 2220478 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[CH:11]=[C:12]([C:15]#[N:16])[NH:13][CH:14]=2)[CH:5]=[CH:6][CH:7]=1.S([O-])([O-])(=O)=[O:18].[Mg+2].C(=O)(O)[O-].[Na+].[O-][Mn](=O)(=O)=O.[K+].[OH2:34]>CC(C)=O.CCOC(C)=O.C(OCC)(=O)C.CCCCCC>[Br:1][C:2]1[CH:3]=[C:4]([C:8](=[O:18])[C:9]([C:10]2[CH:11]=[C:12]([C:15]#[N:16])[NH:13][CH:14]=2)=[O:34])[CH:5]=[CH:6][CH:7]=1

Participants

9

Reactant 5

HCID 962WaterHCID 24083Sulfuric acid magnesium salt (1:1)HCID 516875Potassium PermanganateHCID 516892Sodium BicarbonateHCID 686993714-(3-bromo-phenylethynyl)-1H-pyrrole-2-carbonitrile

Product 1

HCID 587922704-[2-(3-bromophenyl)-2-oxo-acetyl]-1H-pyrrole-2-carbonitrileYield 84%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

A solution of 4-(3-bromo-phenylethynyl)-1H-pyrrole-2-carbonitrile (2.85 g, 10.52 mmol) in acetone was treated with a 45° C. solution of magnesium sulfate (1.90 g, 15.78 mmol) and sodium bicarbonate (0.53 g, 6.31 mmol) in water, immediately treated with KMnO4 (3.74 g, 23.67 mmol), stirred for 15 minutes (TLC (silica gel, 25% ethyl acetate/hexane) indicated complete clean conversion), diluted with EtOAc and washed with water until the washings were colorless. The organic phase was dried (MgSO4), filtered and evaporated. The resultant residue was crystallized to purity from warm ethyl acetate/hexane to afford 4-[2-(3-bromophenyl)-2-oxo-acetyl]-1H-pyrrole-2-carbonitrile as a yellow crystalline solid, 2.68 g, 84% yield.

Workup

  1. washwashed with water until the washings
  2. dry with materialThe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe resultant residue was crystallized to purity
  6. temperaturefrom warm ethyl acetate/hexane

Sources & evidence

ORD record
ord-52f72ed38a5547e8a3020da45c1fb7d3
Source dataset
uspto-grants-2008_08
Patent number
US07417047B2

Reaction notes

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