Hydrochloric Acid → HCID 49765293, Verbindung

HRID 537670Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 537670
C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Br:13][C:14]1[CH:15]=[CH:16][C:17]([CH2:21][CH3:22])=[C:18]([Pb+3])[CH:19]=1.[C:23]1(=[O:30])[CH2:28][CH2:27][CH2:26][C:25](=[O:29])[CH2:24]1.C1(C)C=CC=CC=1.Cl>C(Cl)(Cl)Cl.CN(C)C1C=CN=CC=1>[Br:13][C:14]1[CH:15]=[CH:16][C:17]([CH2:21][CH3:22])=[C:18]([CH:24]2[C:25](=[O:29])[CH2:26][CH2:27][CH2:28][C:23]2=[O:30])[CH:19]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 104341,3-CyclohexanedioneHCID 178476533HCID 178476533, Verbindung

Produkt 1

HCID 49765293HCID 49765293, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 5-bromo-2-ethylphenyllead triacetate (20.00 g, 35.2 mmol) (described in WO08/071,405) in chloroform (100 ml) is added cyclohexane-1,3-dione (3.94 g, 35.2 mmol) and 4-dimethylaminopyridine (22.36 g, 176 mmol). After stirring the reaction at room temperature for 5 minutes toluene (50 ml) is added and the solution is heated at 80° C. for 4 hours. After cooling to room temperature the mixture is allowed to stand overnight, followed by treatment with 2M aqueous hydrochloric acid. Following filtration of the precipitate the biphasic solution is separated, and the aqueous phase is extracted again with dichloromethane (×2). Organic fractions are combined then evaporated under reduced pressure to yield a crude product which is purified by flash column chromatography (10% ethyl acetate/hexane to 70% ethyl acetate/hexane eluant) to afford 2-(5-bromo-2-ethylphenyl)cyclohexane-1,3-dione as a white solid.

Aufarbeitung

  1. additionis added
  2. temperatureAfter cooling to room temperature the mixture
  3. filtrationfiltration of the precipitate the biphasic solution
  4. customis separated
  5. extractionthe aqueous phase is extracted again with dichloromethane (×2)
  6. customOrganic fractions are combined then evaporated under reduced pressure
  7. customto yield a crude product which
  8. customis purified by flash column chromatography (10% ethyl acetate/hexane to 70% ethyl acetate/hexane eluant)

Quellen und Nachweise

ORD-Eintrag
ord-7d68571fb2e24128991a89d0db4d2ca2
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08865623B2

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