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

HRID 1744483Notes

Reaction equation

HRID 1744483 reaction equation
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

Participants

5

Reactant 3

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

Product 1

HCID 31618451-(4-fluorophenyl)-1H-pyrrole-2-carbaldehydeYield 36.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-54b9beed2ae3471aa8691c5ca9cb7251
Source dataset
uspto-grants-2006_03
Patent number
US07015218B1

Reaction notes

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