Acetic Acid → Ethyl 2,4-dichloro-5-fluorobenzoylacetate

HRID 248500

Reaction equation

HRID 248500 reaction equation
[H-].[Na+].C(O[C:6](=[O:10])[O:7][CH2:8][CH3:9])C.[C:11]([C:14]1[C:19]([Cl:20])=[CH:18][C:17]([Cl:21])=[C:16]([F:22])[CH:15]=1)(=[O:13])[CH3:12].C(O)(=O)C>CCOCC>[Cl:20][C:19]1[CH:18]=[C:17]([Cl:21])[C:16]([F:22])=[CH:15][C:14]=1[C:11]([CH2:12][C:6]([O:7][CH2:8][CH3:9])=[O:10])=[O:13]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7766Diethyl CarbonateHCID 24758Sodium hydrideHCID 727250Acetophenone, 2',4'-dichloro-5'-fluoro-

Product 1

HCID 2774350Ethyl 2,4-dichloro-5-fluorobenzoylacetateYield 45%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension of prewashed sodium hydride (76.8 g) in ether was added 189 g of diethylcarbonate. The mixture was heated to reflux and a solution of 131.84 g of 6-acetyl-1,3-dichloro-4-fluorobenzene in 1500 ml of ether was added dropwise over 5 hours. The mixture was then refluxed 24 hours, cooled, poured onto a mixture of ice and acetic acid and extracted several times with ether. The ether extracts were combined, washed with water, dried and evaporated. The residue was purified by vacuum distillation giving 80 g of ethyl 2,4-dichloro-5-fluorobenzoylacetate.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. temperatureThe mixture was then refluxed 24 hours
  4. temperaturecooled
  5. extractionextracted several times with ether
  6. washwashed with water
  7. customdried
  8. customevaporated
  9. distillationThe residue was purified by vacuum distillation

Sources & evidence

ORD record
ord-27c25f8a47ee49479ecdd224e997d1c6
Source dataset
uspto-grants-1993_05
Patent number
US05210193

Linked notes

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