Sodium Carbonate → 2,6-Bis(1,2-diphenyl-1h-benzimidazol-5-yl)-9,10-di(2-naphthyl)anthracene

HRID 1172783Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1172783
Br[C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[C:5]([C:27]3[CH:36]=[CH:35][C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH:28]=3)[C:6]3[C:11]([C:12]=2[C:16]2[CH:25]=[CH:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH:17]=2)=[CH:10][C:9](Br)=[CH:8][CH:7]=3)[CH:3]=1.[C:37]1([N:43]2[C:47]3[CH:48]=[CH:49][C:50](B(O)O)=[CH:51][C:46]=3[N:45]=[C:44]2[C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.COCCOC>[C:37]1([N:43]2[C:47]3[CH:48]=[CH:49][C:50]([C:2]4[CH:15]=[CH:14][C:13]5[C:4](=[C:5]([C:27]6[CH:36]=[CH:35][C:34]7[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=7)[CH:28]=6)[C:6]6[C:11]([C:12]=5[C:16]5[CH:25]=[CH:24][C:23]7[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=7)[CH:17]=5)=[CH:10][C:9]([C:50]5[CH:49]=[CH:48][C:47]7[N:43]([C:37]8[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=8)[C:44]([C:55]8[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=8)=[N:45][C:46]=7[CH:51]=5)=[CH:8][CH:7]=6)[CH:3]=4)=[CH:51][C:46]=3[N:45]=[C:44]2[C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 224978022,6-Dibromo-9,10-di(naphthalen-2-yl)anthraceneHCID 23160233(1,2-diphenyl-1H-benzimidazol-5-yl)Boronic acid

Produkt 1

HCID 231602222,6-Bis(1,2-diphenyl-1h-benzimidazol-5-yl)-9,10-di(2-naphthyl)anthraceneAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

2.0 g (3.4 mmol) of 2,6-dibromo-9,10-di(2-naphthyl)anthracene, 2.4 g (7.5 mmol) of 1,2-diphenyl-1H-benzimidazole-5-boronic acid, and 0.16 g (0.14 mmol) of tetrakis(triphenylphosphine)palladium were dissolved into 30 mL of 1,2-dimethoxyethane. Then, 15 mL of a 2 M aqueous solution of sodium carbonate were added, and the whole was refluxed under heating for 8 hours in an argon atmosphere. The resultant was stood to cool. After the completion of the reaction, the resultant was filtered, and the resultant solid was washed with water, methanol, and toluene to obtain 2.4 g of a greenish white crystal (73% yield). Mass spectral analysis confirmed that the crystal was a target product. The crystal had an m/e of 966 with respect to a molecular weight of 966.37.

Aufarbeitung

  1. temperaturethe whole was refluxed
  2. temperatureunder heating for 8 hours in an argon atmosphere
  3. temperatureto cool
  4. customAfter the completion of the reaction
  5. filtrationthe resultant was filtered
  6. washthe resultant solid was washed with water, methanol, and toluene

Quellen und Nachweise

ORD-Eintrag
ord-3280304f7a004b54a8c3124381f014b7
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07833632B2

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