Potassium Carbonate → 1-(4-fluorophenyl)-1H-pyrrole-2-carbaldehyde

HRID 1744483Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1744483
P(Cl)(Cl)(Cl)=O.[F:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH:17]=[CH:16][CH:15]=[CH:14]2)=[CH:9][CH:8]=1.[C:18](=O)([O-])[O-:19].[K+].[K+]>CN(C)C=O>[F:6][C:7]1[CH:8]=[CH:9][C:10]([N:13]2[CH:17]=[CH:16][CH:15]=[C:14]2[CH:18]=[O:19])=[CH:11][CH:12]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 727844N-(4-fluorophenyl)pyrrole

Produkt 1

HCID 31618451-(4-fluorophenyl)-1H-pyrrole-2-carbaldehydeAusbeute 36,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Phosphorus oxychloride (96.5 g) was added dropwise under ice-cooling to dimethylformamide (600 ml) containing 1-(4-fluorophenyl)pyrrole (101 g) over 1 h, and the mixture was stirred for 2 h and at room temperature for one day. The reaction mixture was added to 3 Liters of aqueous solution containing potassium carbonate (130 g) and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. Diisopropyl ether was added to the residue to allow crystallization. The crystals were recrystallized from a mixed solvent of toluene-diisopropyl ether (ratio=1:10) to give 1-(4-fluorophenyl)-2-formylpyrrole (43 g), melting point: 82–83° C.

Aufarbeitung

  1. additionThe reaction mixture was added to 3 Liters of aqueous solution
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. additionDiisopropyl ether was added to the residue
  7. customcrystallization
  8. customThe crystals were recrystallized from a mixed solvent of toluene-diisopropyl ether (ratio=1:10)

Quellen und Nachweise

ORD-Eintrag
ord-54b9beed2ae3471aa8691c5ca9cb7251
Quelldatensatz
uspto-grants-2006_03
Patentnummer
US07015218B1

Notizen zur Reaktion

Wird geladen…