Dimethyl malonate → 1,3-Dimethyl 2-(4-bromo-2-nitrophenyl)propanedioate

HRID 422032

Reaktionsgleichung

Reaktionsgleichung von HRID 422032
[H-].[Na+].[C:3]([O:10][CH3:11])(=[O:9])[CH2:4][C:5]([O:7][CH3:8])=[O:6].[Br:12][C:13]1[CH:18]=[CH:17][C:16](F)=[C:15]([N+:20]([O-:22])=[O:21])[CH:14]=1>CS(C)=O>[CH3:8][O:7][C:5](=[O:6])[CH:4]([C:16]1[CH:17]=[CH:18][C:13]([Br:12])=[CH:14][C:15]=1[N+:20]([O-:22])=[O:21])[C:3]([O:10][CH3:11])=[O:9]

Komponenten

5

Edukt 3

HCID 7943Dimethyl malonateHCID 24758Sodium hydrideHCID 27363284-Bromo-1-fluoro-2-nitrobenzene

Produkt 1

HCID 157405961,3-Dimethyl 2-(4-bromo-2-nitrophenyl)propanedioate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a suspension of NaH (60% in mineral oil, 972 mg, 24.3 mmol) in DMSO (16 mL) is added dimethyl malonate (2.78 mL, 24.3 mmol). The mixture is heated at 60° C. for 10 min and then is cooled to room temperature before 4-bromo-1-fluoro-2-nitro-benzene (1.0 mL, 8.1 mmol) is added. The resulting mixture is heated at 60° C. for 3 hr and then is quenched with saturated aqueous NH4Cl solution. The mixture is extracted with EtOAc, washed with brine, dried over MgSO4, and concentrated. The crude is used without further purification.

Aufarbeitung

  1. additionis added
  2. temperatureThe resulting mixture is heated at 60° C. for 3 hr
  3. customis quenched with saturated aqueous NH4Cl solution
  4. extractionThe mixture is extracted with EtOAc
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe crude is used without further purification

Quellen und Nachweise

ORD-Eintrag
ord-c24f09dbbd18411d807358b383b3f8db
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08101608B2

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