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

HRID 414267

Reaktionsgleichung

Reaktionsgleichung von HRID 414267
[H-].[Na+].[C:3]([O:10][CH3:11])(=[O:9])[CH2:4][C:5]([O:7][CH3:8])=[O:6].Br[C:13]1[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][C:14]=1[N+:20]([O-:22])=[O:21].[Cl-].[NH4+]>CS(C)=O>[Br:19][C:16]1[CH:17]=[CH:18][C:13]([CH:4]([C:3]([O:10][CH3:11])=[O:9])[C:5]([O:7][CH3:8])=[O:6])=[C:14]([N+:20]([O-:22])=[O:21])[CH:15]=1

Komponenten

6

Edukt 4

HCID 7943Dimethyl malonateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 770041,4-Dibromo-2-nitrobenzene

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To 9.4 g of sodium hydride was added 195 ml of dimethyl sulfoxide, followed by the dropwise addition of 22.37 ml of dimethyl malonate. At the end of the addition, the mixture was heated at 100° C. and maintained at that temperature for 40 minutes. At this point, 25 g of 1,4-dibromo-2-nitrobenzene was added all at once. The reaction mixture was maintained at 100° C. for 4 hours and then it was added to 1.0 liter of saturated ammonium chloride solution. The resulting mixture was extracted with ethyl acetate and the extracts were washed with ammonium chloride solution, water and saturated sodium chloride. The dried (MgSO4) solvent was evaporated, and the residue was recrystalized from ethyl acetate-hexane to give 22.45 g of dimethyl 2-(4-bromo-2-nitrophenyl)malonate.

Aufarbeitung

  1. additionAt the end of the addition
  2. temperaturemaintained at that temperature for 40 minutes
  3. temperatureThe reaction mixture was maintained at 100° C. for 4 hours
  4. extractionThe resulting mixture was extracted with ethyl acetate
  5. washthe extracts were washed with ammonium chloride solution, water and saturated sodium chloride
  6. dry with materialThe dried (MgSO4) solvent
  7. customwas evaporated
  8. customthe residue was recrystalized from ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-3d5eb43172a14b90bf1cd55080bc599b
Quelldatensatz
uspto-grants-1988_12
Patentnummer
US04791131

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