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

HRID 1748491Notes

Reaction equation

HRID 1748491 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-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Phosphoryl chloride (136.3 g) was slowly added dropwise to a solution of 1-(4-fluorophenyl)pyrrole (136.3 g) in N,N-dimethylformamide (250 ml) under ice cooling so as to keep the temperature of the reaction solution under 50° C., and then the mixture was stirred at room temperature for 24 hours. The reaction solution was made alkaline by pouring into an aqueous solution of potassium carbonate under ice cooling and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and concentrated in vacuo. n-Hexane was added to the residue and the resulting precipitated solid was collected by filtration to give 1-(4-fluorophenyl)-2-formylpyrrole (152 g).

Workup

  1. customunder 50° C.
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. concentrationconcentrated in vacuo
  5. additionn-Hexane was added to the residue
  6. customthe resulting precipitated solid
  7. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-f22d06d5a2ed445c98cecb68b2a8e0d8
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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