Diethyl Malonate → HCID 71283960, compound

HRID 2202311Notes

Reaction equation

HRID 2202311 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].[F:14][C:15]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[C:17]([F:24])[C:16]=1F.[Cl-].[NH4+]>C1COCC1>[F:14][C:15]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[C:17]([F:24])[C:16]=1[CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8]

Participants

6

Reactant 4

HCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 27827931,2,3-Trifluoro-5-nitrobenzene

Product 1

HCID 71283960HCID 71283960, compoundYield 94.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl malonate (44.8 g, 280 mmol) was added to a suspension of sodium hydride (60%, oil, 28.0 g, 700 mmol) in THF (280 mL) at 0° C., and the mixture was stirred at room temperature for 1 hr. Then, 1,2,3-trifluoro-5-nitrobenzene (24.79 g, 140 mmol) was added thereto at 0° C., and the mixture was stirred at room temperature for 2 hr. To the reaction mixture was added aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate (×2). The organic layer was washed with brine, and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure to give diethyl 2,6-difluoro-4-nitrophenylmalonate (42 g) as a colorless oil.

Workup

  1. stirringat 0° C., and the mixture was stirred at room temperature for 2 hr
  2. extractionthe mixture was extracted with ethyl acetate (×2)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-64793b4caeeb4c15adb700443bf1a7a3
Source dataset
uspto-grants-2016_06
Patent number
US09365520B2

Reaction notes

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