Sulfuric Acid → HCID 14052571, compound

HRID 330080Notes

Reaction equation

HRID 330080 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]([CH3:23])=[C:21]([F:24])[C:20]([F:25])=[CH:19][C:15]=1[C:16](Cl)=[O:17].S(=O)(=O)(O)O>C1(C)C=CC=CC=1.C(O)C.C(Cl)(Cl)(Cl)Cl>[F:13][C:14]1[C:22]([CH3:23])=[C:21]([F:24])[C:20]([F:25])=[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 5462224MagnesiumHCID 140525702,4,5-Trifluoro-3-methylbenzoyl chloride

Product 1

HCID 14052571HCID 14052571, compoundYield 112.7%

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 1140TolueneSolvent2×HCID 5943Carbon TetrachlorideSolvent

Procedure

To a mixture of magnesium turnings (0.69 g) and absolute ethanol (4.7 ml) was added carbon tetrachloride (0.4 ml). To the stirring suspension was added a solution of diethyl malonate (4.41 g) and absolute ethanol (4.7 ml) in anhydrous toluene (19.2 ml) dropwise during 10 minutes at 15° to 50° C. After the mixture was stirred at 50° to 60° C. for 2 hours, to the mixture was added a solution of 2,4,5-trifluoro-3-methylbenzoyl chloride (4.51 g) in anhydrous toluene (6.4 ml) dropwise at -16° to -13° C. during 10 minutes. The reacting mixture was stirred at -20° C. for 1 hour, and then warmed gradually to room temperature during 1.5 hours with stirring. To this solution was added ice water (25 ml) containing concentrated sulfuric acid (0.8 ml), extracted with toluene. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium chloride and concentrated under reduced pressure to give the title compound (8.10 g).

Workup

  1. stirringThe reacting mixture was stirred at -20° C. for 1 hour
  2. stirringwith stirring
  3. extractionextracted with toluene
  4. washThe organic layer was washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium chloride
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0b1f87e24368493586440c74790c866e
Source dataset
uspto-grants-1990_01
Patent number
US04894458

Reaction notes

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