Dodecane → HCID 86679355, Verbindung

HRID 532316Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 532316
[CH3:1][C:2]1([CH3:35])[C:15]2[CH:14]=[C:13]([C:16]3[CH:21]=[CH:20][C:19]([N:22]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:18][CH:17]=3)[CH:12]=[CH:11][C:10]=2[NH:9][C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.Br[C:37]1[CH:49]=[CH:48][C:47]2[C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[C:40]([CH3:51])([CH3:50])[C:39]=2[CH:38]=1.C(=O)([O-])[O-].[K+].[K+].S(=O)(O)[O-].[Na+].CCCCCCCCCCCC>[Cu].CO.C1(C)C=CC=CC=1>[CH3:50][C:40]1([CH3:51])[C:41]2[CH:42]=[C:43]([N:9]3[C:8]4[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=4)[C:2]([CH3:35])([CH3:1])[C:15]4[CH:14]=[C:13]([C:16]5[CH:21]=[CH:20][C:19]([N:22]([C:23]6[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=6)[C:29]6[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=6)=[CH:18][CH:17]=5)[CH:12]=[CH:11][C:10]3=4)[CH:44]=[CH:45][C:46]=2[C:47]2[C:39]1=[CH:38][CH:37]=[CH:49][CH:48]=2

Komponenten

9

Edukt 5

HCID 8182DodecaneHCID 11430Potassium CarbonateHCID 109456062-Bromo-9,9-dimethylfluoreneHCID 23665763Sodium BisulfiteHCID 86679356HCID 86679356, Verbindung

Produkt 1

HCID 86679355HCID 86679355, VerbindungAusbeute 33,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23978CopperKatalysatorHCID 887MethanolLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
200 °C

Versuchsvorschrift

[4-(9,9-Dimethylacridan-2-yl)phenyl]-diphenylamine (2.02 g), 2-bromo-9,9-dimethyl-9H-fluorene (1.37 g), a copper powder (0.036 g), potassium carbonate (0.94 g), sodium bisulfite (0.078 g), and dodecane (4 ml) were added to a nitrogen-substituted reaction vessel and stirred at 200° C. for 35 hours. The mixture was allowed to cool to a room temperature, and toluene (30 ml) and methanol (30 ml) were added. Precipitated insoluble matter was removed by filtration and concentrated under reduced pressure to obtain a black crude product. The crude product was purified by column chromatography (carrier: silica gel; eluent: hexane/toluene), crystallized with diisopropyl ether/methanol, and then crystallized with ethyl acetate/diisopropyl ether/hexane to obtain a pale yellowish white powder of {4-[10-(9,9-dimethyl-9H-fluorene-2-yl)-9,9-dimethylacridan-2-yl]phenyl}-diphenylamine (0.96 g; yield 33%).

Aufarbeitung

  1. temperatureto cool to a room temperature
  2. customPrecipitated insoluble matter was removed by filtration
  3. concentrationconcentrated under reduced pressure
  4. customto obtain a black crude product
  5. customThe crude product was purified by column chromatography (carrier: silica gel; eluent: hexane/toluene)
  6. customcrystallized with diisopropyl ether/methanol
  7. customcrystallized with ethyl acetate/diisopropyl ether/hexane

Quellen und Nachweise

ORD-Eintrag
ord-46b647691a574dfda517b72099e095e3
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08852759B2

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