Sodium Carbonate → 1-[4-[9,10-di(2-naphtyl)anthracen-2-yl]phenyl]-2-phenyl-1H-benzimidazole

HRID 1172776Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1172776
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[N:10]=[C:9]2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:4][CH:3]=1.[CH:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][C:24]=1[C:33]1[C:34]2[C:39]([C:40]([C:50]3[CH:59]=[CH:58][C:57]4[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=4)[CH:51]=3)=[C:41]3[C:46]=1[CH:45]=[C:44](B(O)O)[CH:43]=[CH:42]3)=[CH:38][CH:37]=[CH:36][CH:35]=2.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>[CH:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][C:24]=1[C:33]1[C:34]2[C:39]([C:40]([C:50]3[CH:59]=[CH:58][C:57]4[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=4)[CH:51]=3)=[C:41]3[C:46]=1[CH:45]=[C:44]([C:2]1[CH:3]=[CH:4][C:5]([N:8]4[C:12]5[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=5[N:10]=[C:9]4[C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)=[CH:6][CH:7]=1)[CH:43]=[CH:42]3)=[CH:38][CH:37]=[CH:36][CH:35]=2

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 230940711-(4-Bromophenyl)-2-phenyl-1H-benzimidazoleHCID 23160220(9,10-Di(naphthalen-2-yl)anthracen-2-yl)boronic acid

Produkt 1

HCID 231602351-[4-[9,10-di(2-naphtyl)anthracen-2-yl]phenyl]-2-phenyl-1H-benzimidazoleAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

1.0 g (2.9 mmol) of 1-(4-bromophenyl)-2-phenyl-1H-benzimidazole, 1.5 g (3.2 mmol) of 9,10-di(2-naphtyl)anthracene-2-boronic acid, and 0.067 g (0.058 mmol) of tetrakis(triphenylphosphine)palladium were dissolved into 20 mL of 1,2-dimethoxyethane. Then, 10 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. After the completion of the reaction, the resultant was filtered, and the resultant solid was washed with water, methanol, and toluene to obtain 1.7 g of a greenish white solid (84% yield). Mass spectral analysis confirmed that the solid was a target product. The solid had an m/e of 698 with respect to a molecular weight of 698.27.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-a9662bc92d79432f84fec3cddf915d34
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07833632B2

Notizen zur Reaktion

Wird geladen…