4-Chlorophthalic anhydride → 1,3-Isobenzofurandione, 5-fluoro-

HRID 1758569Notes

Reaction equation

HRID 1758569 reaction equation
[F-:1].[K+].Cl[C:4]1[CH:5]=[C:6]2[C:11](=[O:12])[O:10][C:8](=[O:9])[C:7]2=[CH:13][CH:14]=1>>[F:1][C:4]1[CH:5]=[C:6]2[C:11](=[O:12])[O:10][C:8](=[O:9])[C:7]2=[CH:13][CH:14]=1

Participants

3

Reactant 2

HCID 670444-Chlorophthalic anhydrideHCID 522689Potassium Fluoride

Product 1

HCID 675721,3-Isobenzofurandione, 5-fluoro-

Conditions

Temperature
220 °C

Procedure

A mixture of 20 parts of anhydrous potassium fluoride, 20 parts of 4-chlorophthalic anhydride and 2 parts of Carbowax® m-peg 2000 catalyst was charged to a reaction vessel and heated at 220° C. for about 18 hours. The product was removed by distillation, then recrystallized from a chloroform-hexane solution to yield 8.13 parts of 4-fluorophthalic anhydride having a melting point of 76°-78° C. Following the procedure of Example 3B, the fluorophthalic anhydride is reacted with ammonia to yield the ammonium salts of a mixed 4- and 5-fluorophthalamic acid.

Workup

  1. additionwas charged to a reaction vessel
  2. customThe product was removed by distillation
  3. customrecrystallized from a chloroform-hexane solution

Sources & evidence

ORD record
ord-2fbf8c36d8274f3c8831ffcb9a69002b
Source dataset
uspto-grants-1983_02
Patent number
US04374266

Reaction notes

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