Hexafluoroacetone trihydrate → HCID 12831594, compound

HRID 2058663Notes

Reaction equation

HRID 2058663 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][CH:10]=[CH: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.O.O.O.[F:23][C:24]([F:32])([F:31])[C:25]([C:27]([F:30])([F:29])[F:28])=[O:26]>C1(C)C=CC=CC=1.O.O.O.FC(F)(F)C(C(F)(F)F)=O>[F:19][C:16]1[CH:17]=[CH:18][C:13]([C:12]2[CH:11]=[C:10]([C:25]([C:27]([F:30])([F:29])[F:28])([C:24]([F:32])([F:31])[F:23])[OH:26])[NH:9][C:8]=2[C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 36719Hexafluoroacetone trihydrateHCID 111079192,3-bis(4-fluorophenyl)-1H-pyrrole

Product 1

HCID 12831594HCID 12831594, compoundYield 63.8%

Reagents, catalysts & solvents 2

HCID 36719Hexafluoroacetone trihydrateCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 20.4 g (0.08 mole) of 2,3-bis(4-fluorophenyl)-1H-pyrrole and 19.8 g (0.09 mole) of hexafluoroacetone trihydrate in 300 ml toluene was heated at reflux for 6 hours. Analysis by tlc indicated a small amount of starting material remained so another 1.0 g of hexafluoroacetone trihydrate was added and the mixture was refluxed another 0.5 hour. After stirring at room temperature overnight, the mixture was concentrated by rotary evaporation. The residue was purified by chromatography on 2 pounds of silica gel, eluting with toluene. The chromatographed product was decolorized with charcoal, then recrystallized from hexane to give 21.5 g (63%) of product, m.p. 112°-113°.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 6 hours
  3. additionwas added
  4. temperaturethe mixture was refluxed another 0.5 hour
  5. concentrationthe mixture was concentrated by rotary evaporation
  6. customThe residue was purified by chromatography on 2 pounds of silica gel
  7. washeluting with toluene
  8. customrecrystallized from hexane

Sources & evidence

ORD record
ord-7382259b826e4746b4134c2b01c38d12
Source dataset
uspto-grants-1982_03
Patent number
US04318917

Reaction notes

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