Sodium hydride → HCID 86644371, Verbindung

HRID 219761

Reaktionsgleichung

Reaktionsgleichung von HRID 219761
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5](F)=[CH:4][C:3]=1[Cl:12].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]([O:23][CH3:24])=[O:22])=[CH:16][CH:15]=1.[H-].[Na+].[NH4+].[Cl-]>CN(C=O)C>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([CH:20]([C:5]2[CH:4]=[C:3]([Cl:12])[C:2]([Cl:1])=[CH:7][C:6]=2[N+:8]([O-:10])=[O:9])[C:21]([O:23][CH3:24])=[O:22])=[CH:18][CH:19]=1

Komponenten

6

Edukt 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 104196Methyl 4-chlorophenylacetateHCID 5339511,2-Dichloro-4-fluoro-5-nitrobenzene

Produkt 1

HCID 86644371HCID 86644371, VerbindungAusbeute 336,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
-5 °C

Versuchsvorschrift

A solution of 5 g of 1,2-dichloro-4-fluoro-5-nitrobenzene and 4.4 g of methyl 4-chlorophenylacetate in 70 ml of DMF is added, under a stream of nitrogen, to a suspension at −10° C. of 2.85 g of 60% NaH in 45 ml of DMF, and the temperature is maintained at −5° C. The mixture is reacted for 2 hours, while allowing the temperature to return to room temperature. The resulting mixture is poured onto ice, aqueous 10% NH4Cl solution is added and the mixture is extracted with ethyl acetate. The organic phase is dried, filtered and concentrated. 30 g of a brown oil are obtained, and are purified on a column with hexane and then with a 95/5 hexane/EtOAc mixture to give 3.18 g of oil.

Aufarbeitung

  1. customThe mixture is reacted for 2 hours
  2. customto return to room temperature
  3. additionis added
  4. extractionthe mixture is extracted with ethyl acetate
  5. customThe organic phase is dried
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d3e024f642e44fe9ba56d7c4d6cdcc3b
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202871B2

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