Hydrochloric Acid → 1,3-Isobenzofurandione, 5-fluoro-

HRID 1076238Notes

Reaction equation

HRID 1076238 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+].Cl>CS(C)=O>[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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2309764-Nitrophthalic acid anhydrideHCID 522689Potassium Fluoride

Product 1

HCID 675721,3-Isobenzofurandione, 5-fluoro-Yield 35%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a reaction vessel fitted with a reflux condenser magnetic stirrer and nitrogen inlet were placed 3.35 grams (0.0174 mol) 4-nitrophthalic anhydride, 2.83 grams (0.036 mol) anhydrous potassium fluoride, and 8 ml. dry dimethyl sulfoxide. The reaction vessel was placed in an oil bath at 142°C. and kept at this temperature for about 35 minutes while stirring the reaction mixture. VPC analysis of a portion of the reaction mixture showed that the reaction was complete after about 20 minutes. The reaction mixture was cooled to room temperature and then poured into dilute aqueous hydrochloric acid and extracted with ethyl acetate to give a product which upon distillation gave 1.007 grams (about 35% yield) of 4-fluorophthalic anhydride.

Workup

  1. customTo a reaction vessel fitted with a reflux condenser magnetic stirrer and nitrogen inlet
  2. customThe reaction vessel was placed in an oil bath at 142°C.
  3. waitwas complete after about 20 minutes
  4. extractionextracted with ethyl acetate
  5. customto give a product which
  6. distillationupon distillation

Sources & evidence

ORD record
ord-0c07365914a54b5594640852bc36b0a6
Source dataset
uspto-grants-1976_05
Patent number
US03956321

Reaction notes

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