Hydrochloric Acid → Diethyl 2-(2-chloro-6-fluorophenyl)malonate

HRID 1348545Notes

Reaction equation

HRID 1348545 reaction equation
[H-].[Na+].[C:3](=[O:10])([O:7][CH2:8][CH3:9])OCC.[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:13]=1[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21].Cl>O1CCCC1>[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:13]=1[CH:19]([C:3]([O:7][CH2:8][CH3:9])=[O:10])[C:20]([O:22][CH2:23][CH3:24])=[O:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7766Diethyl CarbonateHCID 24758Sodium hydrideHCID 2733231Ethyl 2-chloro-6-fluorophenylacetate

Product 1

HCID 2782658Diethyl 2-(2-chloro-6-fluorophenyl)malonateYield 87.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into a mixture of 7.2 g of sodium hydride (60% in oil), 17.0 g of diethyl carbonate and 150 ml of tetrahydrofuran, 26.0 g of ethyl 2-chloro-6-fluorophenylacetate were added dropwise under heating, and then refluxed under heating for 8 hours. The reaction mixture was cooled, poured into iced dil. hydrochloric acid and extracted with t-butyl methyl ether. The organic layer was washed with water, dried over sodium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give 30.4 g of diethyl (2-chloro-6-fluorophenyl)malonate.

Workup

  1. additionwere added dropwise
  2. temperatureunder heating
  3. temperaturerefluxed
  4. temperatureunder heating for 8 hours
  5. temperatureThe reaction mixture was cooled
  6. extractionextracted with t-butyl methyl ether
  7. washThe organic layer was washed with water
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-e37e69539bc748cbb6d02b9052e3096e
Source dataset
uspto-grants-2007_05
Patent number
US07211545B2

Reaction notes

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