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

HRID 463693Notes

Reaction equation

HRID 463693 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-fluorobenzoylmalonate (3) in 50 ml of water. The mixture is heated to boiling, with thorough stirring, for 3 hours, the cooled emulsion is extracted several times with methylene chloride, the combined CH2Cl2 solutions are washed once with saturated NaCl solution, dried with Na2SO4 and the solvent is distilled out in vacuo. Fractionation of the residue under high vacuum provides 21.8 g of ethyl 2,4-dichloro-5-fluorobenzoylacetate (4) of boiling point 127°-142° C./0.09 mbar.

Workup

  1. temperatureThe mixture is heated
  2. extractionthe cooled emulsion is extracted several times with methylene chloride
  3. washthe combined CH2Cl2 solutions are washed once with saturated NaCl solution
  4. dry with materialdried with Na2SO4
  5. distillationthe solvent is distilled out in vacuo

Sources & evidence

ORD record
ord-40340e3f00a343128abe7f7f299ccad7
Source dataset
uspto-grants-1985_10
Patent number
US04544658

Reaction notes

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