Thionyl Chloride → 3,3-Difluorooxolane-2,5-dione

HRID 566959Notes

Reaction equation

HRID 566959 reaction equation
[F:1][C:2]([F:10])([CH2:6][C:7]([OH:9])=[O:8])[C:3](O)=[O:4].S(Cl)(Cl)=O>C1C=CC=CC=1>[F:1][C:2]1([F:10])[CH2:6][C:7](=[O:9])[O:8][C:3]1=[O:4]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 695812,2-Difluorosuccinic acid

Product 1

HCID 131892433,3-Difluorooxolane-2,5-dioneYield 83%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 2,2-difluorosuccinic acid (1.15 g, 7.46 mmol), thionyl chloride (4 mL, 20.6 mmol) and benzene (4 mL) was heated at reflux for 2.5 h. The mixture was filtered and the filtrate was concentrated to afford the title product as an oil that crystallized on standing (838 mg, 6.16 mmol, 83% yield).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2.5 h
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-036ddd05d94a4024a6a0c2a972faa8d2
Source dataset
uspto-grants-2001_01
Patent number
US06177445B1

Reaction notes

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