Sulfuric Acid → Diethyl 6-methyl-2,3,4,5-tetrafluorobenzoylmalonate

HRID 2396949Notes

Reaction equation

HRID 2396949 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].[CH3:13][C:14]1[C:19]([C:20](Cl)=[O:21])=[C:18]([F:23])[C:17]([F:24])=[C:16]([F:25])[C:15]=1[F:26].S(=O)(=O)(O)O>C(Cl)(Cl)(Cl)Cl.C(O)C.C1(C)C=CC=CC=1.O>[CH3:13][C:14]1[C:19]([C:20]([CH:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:2]([O:10][CH2:11][CH3:12])=[O:9])=[O:21])=[C:18]([F:23])[C:17]([F:24])=[C:16]([F:25])[C:15]=1[F:26]

Participants

9

Reactant 4

HCID 1118Sulfuric AcidHCID 7761Diethyl MalonateHCID 5462224MagnesiumHCID 146512562,3,4,5-Tetrafluoro-6-methylbenzoyl chloride

Product 1

HCID 53783746Diethyl 6-methyl-2,3,4,5-tetrafluorobenzoylmalonate

Reagents, catalysts & solvents 4

HCID 5943Carbon TetrachlorideCatalystHCID 702EthanolSolvent2×HCID 962WaterSolventHCID 1140TolueneSolvent2×

Conditions

Temperature
60 °C

Procedure

Separately, two drops of carbon tetrachloride are added to a solution of metallic magnesium (0.56 g) in absolute ethanol (0.9 ml). When the reaction starts, a mixture of diethyl malonate (3.6 ml), absolute ethanol (1.6 ml) and anhydrous toluene (6 ml) is added dropwise below 60° C. After stirring at 60° C. for 1 hour, the reaction mixture is cooled to 0° C. and thereto a solution of 6-methyl-2,3,4,5-tetrafluorobenzoyl chloride (5.00 g) prepared above in toluene (5 ml) is added dropwise. After stirring for 30 minutes, a mixture of conc. sulfuric acid (0.4 ml) and water (6 ml) is added and the mixture is extracted with diethyl ether, and the extract is dried over magnesium sulfate and concentrated to give diethyl 6-methyl-2,3,4,5-tetrafluorobenzoylmalonate (8 g) as an yellow oil.

Workup

  1. additionis added dropwise below 60° C
  2. temperaturethe reaction mixture is cooled to 0° C.
  3. additionis added dropwise
  4. stirringAfter stirring for 30 minutes
  5. additionis added
  6. extractionthe mixture is extracted with diethyl ether
  7. dry with materialthe extract is dried over magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-e885ac672d7741389e70fe03d83da88b
Source dataset
uspto-grants-1996_02
Patent number
US05495020

Reaction notes

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