Potassium Carbonate → HCID 4715098, compound

HRID 1744485Notes

Reaction equation

HRID 1744485 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+]>ClC(Cl)C>[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 63651,1-DichloroethaneSolvent

Procedure

Trifluoromethanesulfonic acid (127 ml) was added dropwise to a dichloroethane solution (680 ml) containing 1-(4-fluorophenyl)-2-formylpyrrole (68 g) at room temperature, and the mixture was stirred at a refluxing temperature for 5 h. After cooling to room temperature, the reaction mixture was poured into aqueous potassium carbonate solution and extracted with chloroform. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, after which the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography (mobile phase:methylene chloride) to give 1-(4-fluorophenyl)-3-formylpyrrole (13 g).

Workup

  1. extractionextracted with chloroform
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customafter which the solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by column chromatography (mobile phase:methylene chloride)

Sources & evidence

ORD record
ord-ba0b7d4cc84341c7ba904a7a10313575
Source dataset
uspto-grants-2006_03
Patent number
US07015218B1

Reaction notes

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