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

HRID 462822Notes

Reaction equation

HRID 462822 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 51%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of 500 parts of 4,4-difluorohexahydrophthalic anhydride and 100 parts of 5 percent Pd/C catalyst in 3615 parts of 1,2,4-trichlorobenzene was charged to an autoclave reactor. The autoclave atmosphere was purged with nitrogen. The autoclave was then sealed, heated to about 250°-285° C. and maintained thereat for about 3.5 hours, then cooled to about room temperature. Analysis of the reaction product by gas chromatographic techniques, indicated a yield of about 51 percent 4-fluorophthalic anhydride, based on the difluorohexahydrophthalic anhydride reactant.

Workup

  1. additionwas charged to an autoclave reactor
  2. customThe autoclave atmosphere was purged with nitrogen
  3. customThe autoclave was then sealed
  4. temperatureheated to about 250°-285° C.
  5. temperaturemaintained
  6. temperaturecooled to about room temperature

Sources & evidence

ORD record
ord-7a715e5aea7c40bd84490c2c2b6c08ca
Source dataset
uspto-grants-1985_05
Patent number
US04517372

Reaction notes

Loading…