p-Toluenesulfonic acid → HCID 14071800, compound

HRID 2232633Notes

Reaction equation

HRID 2232633 reaction equation
[Cl:1][C:2]1[C:20]([Cl:21])=[C:19]([F:22])[C:18]([F:23])=[CH:17][C:3]=1[C:4]([CH:6](C(OCC)=O)[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5].C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[Cl:1][C:2]1[C:20]([Cl:21])=[C:19]([F:22])[C:18]([F:23])=[CH:17][C:3]=1[C:4]([CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 14071801Diethyl (2,3-dichloro-4,5-difluorobenzoyl)propanedioate

Product 1

HCID 14071800HCID 14071800, compoundYield 54.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an emulsion of diethyl 2-(2,3-dichloro-4,5-difluorobenzoyl)malonate (9.71 g) in water (11.2 ml) was added p-toluenesulfonic acid (11.2 mg) and refluxed for 3 hours with stirring vigorously. After cooling, the reaction mixture was extracted with dichloromethane. The organic layer was washed with 7% aqueous sodium carbonate solution and then with water successively, dried over anhydrous sodium sulfate and concentrated. The residue was recrystallized from n-hexane to give the title compound (4.24 g) as powdery crystals. mp 52°-53° C.

Workup

  1. temperaturerefluxed for 3 hours
  2. temperatureAfter cooling
  3. extractionthe reaction mixture was extracted with dichloromethane
  4. washThe organic layer was washed with 7% aqueous sodium carbonate solution
  5. dry with materialwith water successively, dried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was recrystallized from n-hexane

Sources & evidence

ORD record
ord-af1a0b5108454488a84e0a2c09cff29b
Source dataset
uspto-grants-1988_11
Patent number
US04788320

Reaction notes

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