Hydrochloric Acid → Diethyl 3-difluoromethoxy-2,4,5-trifluorobenzoylmalonate

HRID 2226485Notes

Reaction equation

HRID 2226485 reaction equation
C([O-])(=O)CC([O-])=O.C(C(CC)(O[Mg+2])C)C.[O-]CC.[Mg+2].[O-]CC.[C:23]([O:31][CH2:32][CH3:33])(=[O:30])[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26].[F:34][CH:35]([F:49])[O:36][C:37]1[C:38]([F:48])=[C:39]([CH:43]=[C:44]([F:47])[C:45]=1[F:46])[C:40](Cl)=[O:41].Cl>C(OCC)C>[F:49][CH:35]([F:34])[O:36][C:37]1[C:38]([F:48])=[C:39]([CH:43]=[C:44]([F:47])[C:45]=1[F:46])[C:40]([CH:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:23]([O:31][CH2:32][CH3:33])=[O:30])=[O:41]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7761Diethyl MalonateHCID 164963Magnesium ethanolateHCID 152829712,4,5-Trifluoro-3-difluoromethoxybenzoyl chloride

Product 1

HCID 15023783Diethyl 3-difluoromethoxy-2,4,5-trifluorobenzoylmalonate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

Meanwhile, a suspension of diethyl ethoxymagnesium malonate in diethyl ether was prepared from a mixture of 2.80 g (0.0238 moles) of magnesium ethoxide and 3.81 g (0.0238 moles) of diethyl malonate in 60 ml of anhydrous diethyl ether by heating under reflux for 1 hour, whilst stirring. A solution of the 3-difluoromethoxy-2,4,5-trifluorobenzoyl chloride prepared as described above in 50 ml of anhydrous diethyl ether was then added dropwise to the suspension, whilst stirring at room temperature, and the mixture was then stirred at room temperature for an additional 2 hours. 35 ml of 1N aqueous hydrochloric acid were added to the reaction mixture, and the mixture was vigorously stirred. The organic layer was then separated, washed with water and dried over anhydrous sodium sulfate. The solvent was then removed by evaporation under reduced pressure to give 7.07 g of diethyl 3-difluoromethoxy-2,4,5-trifluorobenzoylmalonate [(XIV), R1 =--OCHF2, R3' =H, R17 =C2H5, X=X'=F] as a brown liquid.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 1 hour
  3. additionwas then added dropwise to the suspension
  4. stirringwhilst stirring at room temperature
  5. stirringthe mixture was then stirred at room temperature for an additional 2 hours
  6. stirringthe mixture was vigorously stirred
  7. customThe organic layer was then separated
  8. washwashed with water
  9. dry with materialdried over anhydrous sodium sulfate
  10. customThe solvent was then removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-9b22b8b2e9884ea4837e15fb9f8d9731
Source dataset
uspto-grants-1994_09
Patent number
US05348961

Reaction notes

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