p-Toluenesulfonic acid → Ethyl 2-(3-bromo-2-chloro-4,5-difluorobenzoyl)acetate

HRID 2232635Notes

Reaction equation

HRID 2232635 reaction equation
[Br:1][C:2]1[C:3]([Cl:23])=[C:4]([CH:18]=[C:19]([F:22])[C:20]=1[F:21])[C:5]([CH:7](C(OCC)=O)[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[O:6].C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[Br:1][C:2]1[C:3]([Cl:23])=[C:4]([CH:18]=[C:19]([F:22])[C:20]=1[F:21])[C:5]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[O:6]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 14071798Diethyl 2-(3-bromo-2-chloro-4,5-difluorobenzoyl)malonate

Product 1

HCID 14071799Ethyl 2-(3-bromo-2-chloro-4,5-difluorobenzoyl)acetateYield 48.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an emulsion of diethyl 2-(3-bromo-2-chloro-4,5-difluorobenzoyl)malonate (11.44 g) in water (16 ml) was added p-toluenesulfonic acid (15 mg) and refluxed for 3 hours with stirring vigorously. After cooling, the reaction mixture was extracted with dichloromethane. The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel chromatography eluting with dichloromethane-n-hexane (1:1) to give the title compound (4.56 g), mp 47°-51° 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 water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with dichloromethane-n-hexane (1:1)

Sources & evidence

ORD record
ord-6e7b985b56334e989f4dd9c101437b89
Source dataset
uspto-grants-1988_11
Patent number
US04788320

Reaction notes

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