Acetic Acid → 4-[3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl]-2-(trifluoromethyl)benzoic acid

HRID 1692573Notes

Reaction equation

HRID 1692573 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2([C:27]([F:30])([F:29])[F:28])[CH2:14][C:13]([C:15]3[CH:22]=[CH:21]C(C#N)=[C:17]([C:23]([F:26])([F:25])[F:24])[CH:16]=3)=[N:12][CH2:11]2)[CH:5]=[C:6]([Cl:9])[C:7]=1[Cl:8].O.[CH3:32][C:33]([OH:35])=[O:34]>OS(O)(=O)=O.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2([C:27]([F:28])([F:30])[F:29])[CH2:14][C:13]([C:15]3[CH:22]=[CH:21][C:32]([C:33]([OH:35])=[O:34])=[C:17]([C:23]([F:24])([F:25])[F:26])[CH:16]=3)=[N:12][CH2:11]2)[CH:5]=[C:6]([Cl:9])[C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 582709654-[3-(3,4,5-Trichlorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl]-2-(trifluoromethyl)benzonitrile

Product 1

HCID 582709924-[3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl]-2-(trifluoromethyl)benzoic acidYield 82%

Reagents, catalysts & solvents 1

HCID 21910475Sulfuric acid hydrate (1:1)Solvent

Procedure

4-[3-(3,4,5-Trichlorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl]-2-(trifluoromethyl)benzonitrile (0.82 g, 1.68 mmol) was dissolved in AcOH and suspended in conc. H2SO4—H2O mixture. The reaction mixture was stirred vigorously and refluxed for 26 hours. The reaction mixture was then poured to a mixture of ice and water. The resulting mixture was then extracted with EtOAc and the organic layer was washed with brine and dried over Na2SO4. The solvent was evaporated to obtain the product (0.70 g, 82%).

Workup

  1. temperaturerefluxed for 26 hours
  2. extractionThe resulting mixture was then extracted with EtOAc
  3. washthe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-a7337517cb994651b07eec0b46c29035
Source dataset
uspto-grants-2012_04
Patent number
US08158560B2

Reaction notes

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