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

HRID 646263Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 646263
[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

Komponenten

9

Edukt 5

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 180AcetoneLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 21226206Ethyl acetate hexaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-e55ded96fe654b1892f5d05c1823adfc
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07705030B2

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