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

HRID 1788658Notes

Reaction equation

HRID 1788658 reaction equation
[Br:1][C:2]1[CH:20]=[C:19]([F:21])[C:18]([F:22])=[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>[Br:1][C:2]1[CH:20]=[C:19]([F:21])[C:18]([F:22])=[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 14347789Diethyl (2-bromo-4,5-difluorobenzoyl)malonate

Product 1

HCID 13912599Ethyl (2-bromo-4,5-difluorobenzoyl)acetateYield 84.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of diethyl (2-bromo-4,5-difluorobenzoyl)malonate (75.6 g) in water (100 ml) is added p-toluenesulfonic acid (0.3 g), and the mixture is refluxed for 3 hours. After cooling, the reaction mixture is extracted with dichloromethane. The dichloromethane layer is washed with saturated aqueous sodium chloride solution and dried over magnesium sulfate. After distilling off the solvent under reduced pressure, the residue is distilled to give ethyl (2-bromo-4,5-difluorobenzoyl)acetate (52.0 g), b.p. 105°-115° C. (0.15 mmHg).

Workup

  1. temperaturethe mixture is refluxed for 3 hours
  2. temperatureAfter cooling
  3. extractionthe reaction mixture is extracted with dichloromethane
  4. washThe dichloromethane layer is washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. distillationAfter distilling off the solvent under reduced pressure
  7. distillationthe residue is distilled

Sources & evidence

ORD record
ord-b28196377e324dcfbda86271a54c7717
Source dataset
uspto-grants-1987_08
Patent number
US04684648

Reaction notes

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