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

HRID 1076236Notes

Reaction equation

HRID 1076236 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 59.6%

Procedure

Into a reaction vessel were placed 9.944 grams (0.052 mol) 4-nitrophthalic anhydride and 6.618 grams (0.114 mol) anhydrous potassium fluoride. The reaction vessel was closed and the reactants mixed together for several seconds; thereafter the reaction vessel was fitted with a distilling head, receiver, and nitrogen inlet. The reaction mixture was heated under a nitrogen blanket at approximately an increase of 2°/minute until the temperature reached 225°C. (which took about 45 minutes). The reaction mixture was then heated at a temperature of 235°-240°C. for an additional 60 minutes at which time the nitrogen line was replaced by a vacuum line and the pressure lowered until distillation of the reaction mixture began to take place. This resulted in a yield of 5.101 grams (59.6% yield) of 4-fluorophthalic anhydride, boiling point 205°-206°C./160 mm. This material, which on cooling solidified to give a solid melting at 74°-76°C., was identified as essentially pure 4-fluorophthalic anhydride.

Workup

  1. customInto a reaction vessel were placed
  2. customThe reaction vessel was closed
  3. additionthe reactants mixed together for several seconds
  4. customthereafter the reaction vessel was fitted with a distilling head, receiver, and nitrogen inlet
  5. temperatureThe reaction mixture was heated under a nitrogen blanket at approximately
  6. temperaturean increase of 2°/minute until the temperature
  7. customreached 225°C.
  8. custom(which took about 45 minutes)
  9. temperatureThe reaction mixture was then heated at a temperature of 235°-240°C. for an additional 60 minutes at which time the nitrogen line
  10. distillationthe pressure lowered until distillation of the reaction mixture

Sources & evidence

ORD record
ord-dba11d17cf6c4c8b89b828a41a6f4ffc
Source dataset
uspto-grants-1976_05
Patent number
US03956321

Reaction notes

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