p-Toluenesulfonic acid → Ethyl 3-bromo-2,4,5-trifluorobenzoylacetate

HRID 1761650Notes

Reaction equation

HRID 1761650 reaction equation
[Br:1][C:2]1[C:3]([F: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]([F: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 13748803Diethyl 3-bromo-2,4,5-trifluorobenzoylmalonate

Product 1

HCID 10592111Ethyl 3-bromo-2,4,5-trifluorobenzoylacetateYield 56.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an emulsion of diethyl 3-bromo-2,4,5-trifluorobenzoylmalonate (3.25 g) in water (4 ml) was added p-toluenesulfonic acid (4 mg) and refluxed for 3 hours with vigorous stirring. After cooling, the reaction mixture was extracted with dichloromethane (8 ml×4). The organic layer was washed with water saturated with sodium chloride, dried over anhydrous sodium sulfate and concentrated. The residue was recrystallized from dichloromethane-n-hexane to give the title compound (1.51 g), mp 85°-88° C.

Workup

  1. temperaturerefluxed for 3 hours with vigorous stirring
  2. temperatureAfter cooling
  3. extractionthe reaction mixture was extracted with dichloromethane (8 ml×4)
  4. washThe organic layer was washed with water saturated with sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was recrystallized from dichloromethane-n-hexane

Sources & evidence

ORD record
ord-11dcdb26c38a4600b3271fdecf8009a9
Source dataset
uspto-grants-1989_05
Patent number
US04826982

Reaction notes

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