p-Toluenesulfonic acid → Ethyl 2,4-dichloro-5-fluorobenzoylacetate

HRID 1284500Notes

Reaction equation

HRID 1284500 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[Cl:12][C:13]1[CH:31]=[C:30]([Cl:32])[C:29]([F:33])=[CH:28][C:14]=1[C:15]([CH:17](C(OCC)=O)[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:16]>O>[Cl:12][C:13]1[CH:31]=[C:30]([Cl:32])[C:29]([F:33])=[CH:28][C:14]=1[C:15]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:16]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 13326819Diethyl 2-(2,4-dichloro-5-fluorobenzoyl)malonate

Product 1

HCID 2774350Ethyl 2,4-dichloro-5-fluorobenzoylacetateYield 78.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.15 g of p-toluenesulphonic acid is added to an emulsion of 34.9 g of crude diethyl 2,4-dichloro-5-fluoro-benzoyl-malonate in 50 ml of water. The mixture is heated at the boiling point for 3 hours, while stirring well, the cooled emulsion is extracted several times with methylene chloride, the combined methylene chloride solutions are washed once with saturated sodium chloride solution and dried with sodium sulphate and the solvent is distilled off in vacuo. Fractionation of the residue under a fine vacuum gives 21.8 g of ethyl 2,4-dichloro-5-fluoro-benzoylacetate of boiling point 127°-142° C./0.09 mbar.

Workup

  1. temperatureThe mixture is heated at the boiling point for 3 hours
  2. extractionthe cooled emulsion is extracted several times with methylene chloride
  3. washthe combined methylene chloride solutions are washed once with saturated sodium chloride solution
  4. dry with materialdried with sodium sulphate
  5. distillationthe solvent is distilled off in vacuo

Sources & evidence

ORD record
ord-6884a88b086e40a2907c03dc7e656b3a
Source dataset
uspto-grants-1986_01
Patent number
US04563459

Reaction notes

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