1,3-Isobenzofurandione, 5-fluoro- → HCID 57283400, compound

HRID 465742Notes

Reaction equation

HRID 465742 reaction equation
F[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.[C:13]([O-:21])(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Na+]>CN(C=O)C>[C:13]([O:21][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)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 675721,3-Isobenzofurandione, 5-fluoro-HCID 517055Sodium Benzoate

Product 1

HCID 57283400HCID 57283400, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Fluorophthalic anhydride (16.7 g, 100 mmol) and sodium benzoate (14.5 g, 101 mmol) were heated to about 145° C. in DMF (70 ml). After heating for 5 hours, the solvent was distilled off under reduced pressure (the temperature was kept at less than 100° C.). Ethyl acetate (50 ml) was added and the suspension refluxed for 30 minutes. The suspension was filtered and the ethyl acetate allowed to cool to give 4-benzoyloxyphthalic anhydride (13.6 g, 86% pure) as a whitish solid. Ethyl acetate (8 mls) was distilled from the mother liquor and hexane added to the hot solution. The solution was allowed to cool and stand for several days upon which a solid benzoyloxyphthalic anhydride precipitated (4.7 g, 79% pure).

Workup

  1. temperatureAfter heating for 5 hours
  2. distillationthe solvent was distilled off under reduced pressure (the temperature
  3. customwas kept at less than 100° C.
  4. additionEthyl acetate (50 ml) was added
  5. temperaturethe suspension refluxed for 30 minutes
  6. filtrationThe suspension was filtered
  7. temperatureto cool

Sources & evidence

ORD record
ord-3dcd6156856f4698995e577f670f0cb5
Source dataset
uspto-grants-1992_10
Patent number
US05153335

Reaction notes

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