Diethyl methylmalonate → Diethyl 2-(2-bromo-4-nitrophenyl)-2-methylmalonate

HRID 39191

Reaktionsgleichung

Reaktionsgleichung von HRID 39191
[CH3:1][CH:2]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].[Br:15][C:16]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:17]=1F>CN(C=O)C>[Br:15][C:16]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:17]=1[C:2]([CH3:1])([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Komponenten

5

Edukt 3

HCID 11857Diethyl methylmalonateHCID 24758Sodium hydrideHCID 696992-Bromo-1-fluoro-4-nitrobenzene

Produkt 1

HCID 59206132Diethyl 2-(2-bromo-4-nitrophenyl)-2-methylmalonateAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Diethyl 2-methylmalonate (4.31 mL, 25.0 mmol) was dissolved in 25 mL of anhydrous DMF. This solution was cooled to 0° C. under an atmosphere of nitrogen. Sodium hydride (1.04 g, 26 mmol, 60% by weight in mineral oil) was slowly added to the solution. The resulting mixture was allowed to stir for 3 minutes at 0° C., and then at room temperature for 10 minutes. 2-Bromo-1-fluoro-4-nitrobenzene (5.00 g, 22.7 mmol) was quickly added and the mixture turned bright red. After stirring for 10 minutes at room temperature, the crude mixture was evaporated to dryness and then partitioned between dichloromethane and a saturated aqueous solution of sodium chloride. The layers were separated and the organic phase was washed twice with a saturated aqueous solution of sodium chloride. The organics were concentrated to yield diethyl 2-(2-bromo-4-nitrophenyl)-2-methylmalonate (8.4 g, 99%) as a pale yellow oil which was used without further purification. Retention time 1.86 min.

Aufarbeitung

  1. waitat room temperature for 10 minutes
  2. stirringAfter stirring for 10 minutes at room temperature
  3. customthe crude mixture was evaporated to dryness
  4. custompartitioned between dichloromethane
  5. customThe layers were separated
  6. washthe organic phase was washed twice with a saturated aqueous solution of sodium chloride
  7. concentrationThe organics were concentrated

Quellen und Nachweise

ORD-Eintrag
ord-36d28dae0c694402b63d442f4eef0be0
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524767B2

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