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2-(4-Bromophenyl)quinoline → 2-[4,4''-Di(2-quinolyl)-1,1':3',1''-terphenyl-5-yl]-4,6-di-p-tolyl-1,3,5-triazine

HRID 1028918
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1028918
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1.[CH2:18]([Li])[CH2:19][CH2:20][CH3:21].Br[C:24]1[CH:25]=[C:26]([C:31]2[N:36]=[C:35]([C:37]3[CH:42]=[CH:41][C:40]([CH3:43])=[CH:39][CH:38]=3)[N:34]=[C:33]([C:44]3[CH:49]=[CH:48][C:47]([CH3:50])=[CH:46][CH:45]=3)[N:32]=2)[CH:27]=[C:28](Br)[CH:29]=1>O1CCCC1.CCCCCC.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>[N:9]1[C:8]2[C:21](=[CH:2][CH:3]=[CH:4][CH:5]=2)[CH:20]=[CH:19][C:18]=1[C:25]1[C:26]([C:31]2[N:36]=[C:35]([C:37]3[CH:42]=[CH:41][C:40]([CH3:43])=[CH:39][CH:38]=3)[N:34]=[C:33]([C:44]3[CH:49]=[CH:48][C:47]([CH3:50])=[CH:46][CH:45]=3)[N:32]=2)=[CH:27][C:28]([C:15]2[CH:10]=[CH:11][CH:12]=[C:13]([C:2]3[CH:7]=[CH:6][C:5]([C:8]4[CH:17]=[CH:16][C:15]5[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=5)[N:9]=4)=[CH:4][CH:3]=3)[CH:14]=2)=[CH:29][CH:24]=1
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Komponenten

7

Edukt 3

HCID 14734442-(4-Bromophenyl)quinolineHCID 583826282-(3,5-Dibromophenyl)-4,6-di-p-tolyl-1,3,5-triazineHCID 178418339Butyllithium

Produkt 1

HCID 673562442-[4,4''-Di(2-quinolyl)-1,1':3',1''-terphenyl-5-yl]-4,6-di-p-tolyl-1,3,5-triazineAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 8028TetrahydrofuranLösungsmittel2×
HCID 8058HexaneLösungsmittel

Versuchsvorschrift

In a stream of argon, 2.58 g (9.09 mmol) of 2-(4-bromophenyl) quinoline was dissolved in 20 mL of tetrahydrofuran. To the thus-obtained solution, 6.01 mL of a solution in hexane of 9.70 mmol of butyllithium was dropwise added at −78° C. The resultant mixture was stirred at −78° C. for 15 minutes, and then 2.45 g (9.70 mmol) of dichloro(tetramethylethylene-diamine)zinc(II) was added. Temperature of the resultant mixture was elevated to room temperature, and stirred for 1.5 hours. The resultant mixture, and 1.50 g (3.03 mmol) of 2-(3,5-dibromophenyl)-4,6-di-p-tolyl-1,3,5-triazine, and 420 mg (0.364 mmol) of tetrakis(triphenylphosphine)palladium were suspended in 30 mL of tetrahydrofuran, and the obtained suspension was heated under reflux with stirring for 15 hours. The reaction mixture was cooled to room temperature, and was then distilled under a reduced pressure to remove low boiling ingredients. Methanol was added to the concentrate and the thus-deposited solid was filtered. The thus-obtained crude product was purified by silica gel chromatography using a methanol/chloroform (1:100-2:100) mixed liquid as a developing solvent to give 2.03 g of the target 2-[4,4″-di(2-quinolyl)-1,1′:3′,1″-terphenyl-5-yl]-4,6-di-p-tolyl-1,3,5-triazine as a white solid (yield: 90%).

Aufarbeitung

  1. customwas elevated to room temperature
  2. temperaturethe obtained suspension was heated
  3. temperatureunder reflux
  4. stirringwith stirring for 15 hours
  5. distillationwas then distilled under a reduced pressure
  6. customto remove low boiling ingredients
  7. additionMethanol was added to the
  8. concentrationconcentrate
  9. filtrationthe thus-deposited solid was filtered
  10. customThe thus-obtained crude product
  11. customwas purified by silica gel chromatography
  12. additionmixed liquid as a developing solvent

Quellen und Nachweise

ORD-Eintrag
ord-8be869e0c42940d3830baafcdbcb0d6e
Quelldatensatz
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08735577B2

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