Sulfuric Acid → Diethyl (2,3,4-trifluorobenzoyl)malonate

HRID 2209983Notes

Reaction equation

HRID 2209983 reaction equation
[Mg].[C:2]([O:10][CH2:11][CH3:12])(=[O:9])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[F:13][C:14]1[C:22]([F:23])=[C:21]([F:24])[CH:20]=[CH:19][C:15]=1[C:16](Cl)=[O:17].S(=O)(=O)(O)O>C(Cl)(Cl)(Cl)Cl.C(O)C.C1(C)C=CC=CC=1>[F:13][C:14]1[C:22]([F:23])=[C:21]([F:24])[CH:20]=[CH:19][C:15]=1[C:16]([CH:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:2]([O:10][CH2:11][CH3:12])=[O:9])=[O:17]

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 7761Diethyl MalonateHCID 27340222,3,4-Trifluorobenzoyl chlorideHCID 5462224Magnesium

Product 1

HCID 15105382Diethyl (2,3,4-trifluorobenzoyl)malonate

Reagents, catalysts & solvents 3

HCID 5943Carbon TetrachlorideCatalystHCID 702EthanolSolvent2×HCID 1140TolueneSolvent2×

Procedure

3.6 g (0.148 mol) of magnesium filings are introduced into 8.1 ml of ethanol, the reaction is started up using a few drops of carbon tetrachloride, and a solution of 21.8 g (0.136 mol) of diethyl malonate in 15 ml of ethanol and 58 ml of toluene is subsequently added dropwise in such a manner that the internal temperature is between 50 and 60° C. Stirring is subsequently continued for one hour at 60° C. A solution of 27.6 g (0.15 mol) of 2,3,4-trifluorobenzoyl chloride in 15.4 ml of toluene is added dropwise at -10° to -5° C., and stirring is continued for one hour at 0° C. and subsequently overnight, allowing the mixture to come to room temperature. The batch is poured into 60 ml of ice-water, treated with 9.7 ml of concentrated sulphuric acid and extracted using toluene. The toluene phase is washed with saturated sodium chloride solution and the solvent is removed in vacuo.

Workup

  1. customis between 50 and 60° C
  2. stirringstirring
  3. waitis continued for one hour at 0° C. and subsequently overnight
  4. customto come to room temperature
  5. extractionextracted
  6. washThe toluene phase is washed with saturated sodium chloride solution
  7. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-7bf9d42ccb1848f28a0f80e141b94a45
Source dataset
uspto-grants-1995_10
Patent number
US05457104

Reaction notes

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