4-Nitrophthalic acid anhydride → 1,3-Isobenzofurandione, 5-fluoro-

HRID 1076237Notes

Reaction equation

HRID 1076237 reaction equation
[N+]([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)([O-])=O.[F-:15].[K+]>>[F:15][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 2309764-Nitrophthalic acid anhydrideHCID 522689Potassium Fluoride

Product 1

HCID 675721,3-Isobenzofurandione, 5-fluoro-Yield 60%

Conditions

Temperature
100 °C

Procedure

Into a reaction vessel were placed 290 grams (1.5 mol) 4-nitrophthalic anhydride and 91 grams (1.57 mol) of anhydrous potassium fluoride. The reaction vessel was closed and shaken to mix the reactants and was then attached to a distilling head, receiver, and nitrogen inlet. The mixture was heated, under a nitrogen blanket beginning at 100°C. while the temperature was raised to 230°C. over a 25 minute period and kept at a temperature of 230°-250°C. for about 4 hours. After 2 hours, the nitrogen line was replaced by a vacuum line and the system evacuated to about 160 mm. This resulted in the collection over the next 2 hours of 148.5 grams (60% yield) 4-fluorophthalic anhydride, which upon analysis indicated the material to be greater than 97% pure (melting point 72°-76°C.).

Workup

  1. customInto a reaction vessel were placed
  2. customThe reaction vessel was closed
  3. additionto mix the reactants
  4. temperaturewas raised to 230°C. over a 25 minute period
  5. waitAfter 2 hours
  6. customthe system evacuated to about 160 mm

Sources & evidence

ORD record
ord-2a74df891a6a4bdbabc96352a95f99ad
Source dataset
uspto-grants-1976_05
Patent number
US03956321

Reaction notes

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