1,2-Dichloroethane → Ethyl 2,4,5-trifluorobenzoylacetate

HRID 1989796Notes

Reaction equation

HRID 1989796 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([F:10])[C:7]([F:11])=[CH:6][C:3]=1C#N.C([CH:14]([C:18]([O-:20])=O)[C:15]([O-:17])=[O:16])C.[K+].[K+].Cl.Cl[CH2:25][CH2:26]Cl>[Cl-].[Zn+2].[Cl-]>[F:1][C:2]1[CH:9]=[C:8]([F:10])[C:7]([F:11])=[CH:6][C:3]=1[C:18]([CH2:14][C:15]([O:17][CH2:25][CH3:26])=[O:16])=[O:20]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 313Hydrochloric AcidHCID 5938132,4,5-TrifluorobenzonitrileHCID 86617294Potassium ethylmalonate

Product 1

HCID 2758933Ethyl 2,4,5-trifluorobenzoylacetateYield 80%

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Conditions

Temperature
90 °C

Procedure

To 10 □ of 1,2-dichloroethane were added 1.0 g of 2,4,5-trifluorobenzonitrile, 0.43 g of zinc chloride, and 1.3 g of potassium ethylmalonate, and then the mixture was stirred at reflux. After the reaction was completed, 11 □ of 6 N hydrochloric acid was added to the mixture, which then was stirred at reflux at 90° C. for 1 hour. After confirming completion of the reaction by TLC, the solution was cooled to 20° C., and then an organic layer was separated therefrom. The organic layer was concentrated through distillation under reduced pressure. Thus resulted residue was purified by silica gel column chromatography (eluent: ethylacetate/n-hexane=1/10, v/v) to obtain the title compound in the yield of 80% (1.2 g).

Workup

  1. temperatureat reflux
  2. stirringthen was stirred
  3. customcompletion of the reaction by TLC
  4. temperaturethe solution was cooled to 20° C.
  5. customan organic layer was separated
  6. concentrationThe organic layer was concentrated through distillation under reduced pressure
  7. customThus resulted residue was purified by silica gel column chromatography (eluent

Sources & evidence

ORD record
ord-0a34a13c737c42d29ed0201a6542d316
Source dataset
uspto-grants-2010_01
Patent number
US07642356B2

Reaction notes

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