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Sulfuric Acid → Diethyl (2-bromo-4,5-difluorobenzoyl)malonate

HRID 2232078
Notes
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Reaction equation

HRID 2232078 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].[Br:13][C:14]1[CH:22]=[C:21]([F:23])[C:20]([F:24])=[CH:19][C:15]=1[C:16](Cl)=[O:17].S(=O)(=O)(O)O>C(O)C.CCOCC.C(Cl)(Cl)(Cl)Cl>[Br:13][C:14]1[CH:22]=[C:21]([F:23])[C:20]([F:24])=[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 7761Diethyl MalonateHCID 27832942-Bromo-4,5-difluorobenzoyl chlorideHCID 5462224Magnesium

Product 1

HCID 14347789Diethyl (2-bromo-4,5-difluorobenzoyl)malonateYield 108.2%

Reagents, catalysts & solvents 3

HCID 702
Ethanol
Solvent
2×
HCID 3283Diethyl EtherSolvent2×
HCID 5943Carbon TetrachlorideSolvent

Procedure

Magnesium ribbon (7.3 g) is suspended in absolute ethanol (15 ml), and thereto is added carbon tetrachloride (1.5 ml), and thereto is added dropwise a mixture of diethyl malonate (48 g), absolute ethanol (30 ml) and anhydrous ether (120 ml) over a period of one hour. After the addition, the mixture is refluxed for 2 hours. After cooling till room temperature, a solution of 2-bromo-4,5-difluorobenzoyl chloride (92 g) in anhydrous ether (50 ml) is added dropwise to the mixture. After the addition, the mixture is allowed to stand overnight at room temperature. A mixture of ice-water (120 ml) and conc. sulfuric acid (8 ml) is added dropwise to the reaction mixture under ice-cooling. After the addition, the mixture is extracted with ether. The ether layer is washed with saturated aqueous sodium chloride solution and dried over magnesium sulfate. The solvent is distilled off under reduced pressure to give diethyl (2-bromo-4,5-difluorobenzoyl)malonate (123 g).

Workup

  1. additionis added dropwise
  2. additionAfter the addition
  3. temperaturethe mixture is refluxed for 2 hours
  4. additionAfter the addition
  5. additionis added dropwise to the reaction mixture under ice-
  6. temperaturecooling
  7. additionAfter the addition
  8. extractionthe mixture is extracted with ether
  9. washThe ether layer is washed with saturated aqueous sodium chloride solution
  10. dry with materialdried over magnesium sulfate
  11. distillationThe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-24a08def650d4833b3d0ef41a9d2880a
Source dataset
uspto-grants-1988_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04786649

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes