2-Chlorotoluene → 1,3-Isobenzofurandione, 5-fluoro-

HRID 462823Notes

Reaction equation

HRID 462823 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=CC=1C>[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 72382-ChlorotolueneHCID 140082495,5-Difluorohexahydro-2-benzofuran-1,3-dione

Product 1

HCID 675721,3-Isobenzofurandione, 5-fluoro-Yield 37%

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 3787 parts of o-chlorotoluene was charged to an autoclave reactor. The autoclave atmosphere was purged with nitrogen. The autoclave when then sealed, heated to 300°-350° and maintained thereat for about 3 hours, then cooled to about room temperature. Analysis of the reaction product, by gas chromatographic techniques indicated a 37 percent yield of 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 when then sealed
  4. temperatureheated to 300°-350°
  5. temperaturemaintained
  6. temperaturecooled to about room temperature

Sources & evidence

ORD record
ord-40179c84082049ed9cdd852cdd4a12ac
Source dataset
uspto-grants-1985_05
Patent number
US04517372

Reaction notes

Loading…