Potassium Carbonate → HCID 4715098, compound

HRID 1748492Notes

Reaction equation

HRID 1748492 reaction equation
FC(F)(F)S(O)(=O)=O.[F:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH:20]=[CH:19][CH:18]=[C:17]2C=O)=[CH:12][CH:11]=1.[C:23](=O)([O-])[O-:24].[K+].[K+]>ClCCl>[F:9][C:10]1[CH:11]=[CH:12][C:13]([N:16]2[CH:17]=[CH:18][C:19]([CH:23]=[O:24])=[CH:20]2)=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 62406Trifluoromethanesulfonic acidHCID 31618451-(4-fluorophenyl)-1H-pyrrole-2-carbaldehyde

Product 1

HCID 4715098HCID 4715098, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoromethanesulfonic acid (100 g) was added dropwise at room temperature into a dichloromethane solution (680 ml) containing 1-(4-fluorophenyl)-2-formylpyrrole (50.4 g), and stirred at reflux temperature for 13 hours. The reaction solution was poured into ice water, made alkaline with the addition of potassium carbonate and extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified with silica gel column chromatography (n-hexane/ethyl acetate) to give 1-(4-fluorophenyl)-3-formylpyrrole (34.5 g).

Workup

  1. temperatureat reflux temperature for 13 hours
  2. extractionextracted with chloroform
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified with silica gel column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-277d9dd4c88240bcbac2045e55be618a
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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