Sodium Carbonate → 5-Fluoro-1-(4-fluorophenyl)-2-(4-methylsulfonylphenyl)pyrrole

HRID 856828Notes

Reaction equation

HRID 856828 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[CH:11][CH:10]=[C:9]2[C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[Xe](F)[F:24].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[F:24][C:12]1[N:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[C:9]([C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=2)=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 83674Xenon difluorideHCID 108291321-(4-Fluorophenyl)-2-(4-methylsulfonylphenyl)pyrroleHCID 178435160HCID 178435160, compound

Product 1

HCID 218627875-Fluoro-1-(4-fluorophenyl)-2-(4-methylsulfonylphenyl)pyrroleYield 35.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.90 g (2.7 mmol) of 1-(4-fluorophenyl)-2-(4-methylsulfonylphenyl)pyrrole (prepared as described in Example 33) was dissolved in 10 ml of acetonitrile in a reaction vessel made of polyethylene, and 0.46 g (2.7 mmol) of xenon difluoride was added to the resulting solution at 0° C., whilst stirring. The temperature of the reaction mixture was then allowed to return to room temperature, and the mixture was stirred at room temperature for 20 hours. At the end of this time, 20 ml of a saturated aqueous solution of sodium carbonate was added to the mixture, which was then extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium carbonate and then with water, after which it was dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure. The resulting residue was applied to a silica gel chromatography column and eluted with a 3:1 by volume mixture of hexane and ethyl acetate, to give 0.32 g of the title compound as white prismatic crystals (yield 34%), melting at 140-141° C.

Workup

  1. additionwas added to the resulting solution at 0° C.
  2. customto return to room temperature
  3. stirringthe mixture was stirred at room temperature for 20 hours
  4. extractionwas then extracted with ethyl acetate
  5. washThe organic layer was washed with a saturated aqueous solution of sodium carbonate
  6. dry with materialwith water, after which it was dried over anhydrous magnesium sulfate
  7. customThe solvent was then removed by distillation under reduced pressure
  8. washeluted with a 3:1 by volume mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-d63218da6254499d918725cef006e123
Source dataset
uspto-grants-2006_12
Patent number
USRE039420E1

Reaction notes

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