1,2,4-Trichlorobenzene → 1,3-Isobenzofurandione, 5-fluoro-

HRID 462821Notes

Reaction equation

HRID 462821 reaction equation
[F:1][C:2]1(F)[CH2:12][CH2:11][CH:5]2[C:6]([O:8][C:9](=[O:10])[CH:4]2[CH2:3]1)=[O:7].ClC1C=CC(Cl)=CC=1Cl>[Pd]>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[O:10])[O:8][C:6](=[O:7])[C:5]2=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 131,2,4-TrichlorobenzeneHCID 140082495,5-Difluorohexahydro-2-benzofuran-1,3-dione

Product 1

HCID 675721,3-Isobenzofurandione, 5-fluoro-Yield 25%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of 50.0 parts of 4,4-difluorohexahydrophthalic anhydride and 10 parts of 5 percent palladium of carbon (Pd/C) catalyst in 578 parts of 1,2,4-trichlorobenzene was heated to reflux conditions and maintained at reflux for about 16 hours, with stirring. The reaction mixture was then cooled to about room temperature. Analysis of the reaction product using gas chromatographic techniques, indicated a yield of about 25 percent of 4-fluorophthalic anhydride, based on the difluorohexahydrophthalic anhydride reactant.

Workup

  1. temperaturewas heated
  2. temperatureto reflux conditions
  3. temperaturemaintained
  4. temperatureat reflux for about 16 hours
  5. temperatureThe reaction mixture was then cooled to about room temperature

Sources & evidence

ORD record
ord-c68a104204e6427b98c520213301f31e
Source dataset
uspto-grants-1985_05
Patent number
US04517372

Reaction notes

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