HCID 12831594, compound → 4,5-Bis(4-fluorophenyl)-2-[2,2,2-trifluoro-1-(trifluoromethyl)ethylidene]-2H-pyrrole

HRID 2058664Notes

Reaction equation

HRID 2058664 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:20]([C:26]([F:29])([F:28])[F:27])([C:22]([F:25])([F:24])[F:23])O)[NH:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1>C(OC(=O)C)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)=[N:11][C:10](=[C:20]([C:26]([F:29])([F:28])[F:27])[C:22]([F:23])([F:24])[F:25])[CH:9]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 12831594HCID 12831594, compound

Product 1

HCID 128315954,5-Bis(4-fluorophenyl)-2-[2,2,2-trifluoro-1-(trifluoromethyl)ethylidene]-2H-pyrrole

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A mixture of 4.2 g (0.01 mole) of 4,5-bis(4-fluorophenyl)-α,α-di(trifluoromethyl)-1H-pyrrole-2-methanol and 100 ml acetic anhydride was heated at reflux under nitrogen for 3 hours. The mixture was cooled and concentrated under vacuum. The residue was purified by column chromatography on 400 g of silica gel. Eluted with 50/50 hexane/toluene was 4,5-bis(4-fluorophenyl)-2[2,2,2-trifluoro-1-(trifluoromethyl)-ethylidene]-2H-pyrrole, obtained after recrystallization from hexane as a yellow-orange solid, 1.8 g (45%), m.p. 145°-146°. The ir and nmr (proton and fluorine) spectra were consistent with the assigned structure.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for 3 hours
  3. temperatureThe mixture was cooled
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by column chromatography on 400 g of silica gel
  6. washEluted with 50/50 hexane/toluene
  7. customobtained
  8. customafter recrystallization from hexane as a yellow-orange solid, 1.8 g (45%), m.p. 145°-146°

Sources & evidence

ORD record
ord-db91a04b49324546bb9d3896a28a7c7e
Source dataset
uspto-grants-1982_03
Patent number
US04318917

Reaction notes

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