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

HRID 1421417Notes

Reaction equation

HRID 1421417 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×

Conditions

Temperature
60 °C

Procedure

3.6 g (0.148 mol) of magnesium filings are initially introduced into 8.1 ml of ethanol, the reaction is started with 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 then added dropwise such that the internal temperature is between 50 and 60° C. The mixture is then subsequently stirred at 60° C. for one hour. 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 the mixture is subsequently stirred at 0° C. for one hour and then overnight, while warming to room temperature. It is poured onto 60 ml of ice-water, 9.7 ml of concentrated sulphuric acid are added and the mixture is extracted with toluene. The extract is washed with saturated sodium chloride solution and the solvent is removed in vacuo. Crude yield: 45.2 g

Workup

  1. customis between 50 and 60° C
  2. stirringthe mixture is subsequently stirred at 0° C. for one hour
  3. temperatureovernight, while warming to room temperature
  4. additionare added
  5. extractionthe mixture is extracted with toluene
  6. washThe extract is washed with saturated sodium chloride solution
  7. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-817f12b8dfed4992a2dfff0732e371f7
Source dataset
uspto-grants-2000_06
Patent number
US06075165

Reaction notes

Loading…