Toluene → 9-([1,1':3',1''-Terphenyl]-5'-yl)-10-([2,2'-binaphthalen]-7-yl)anthracene

HRID 2179857Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2179857
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[C:12]4[C:17]([C:18](Br)=[C:19]5[C:24]=3[CH:23]=[CH:22][CH:21]=[CH:20]5)=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:26]1[CH:35]=[CH:34][C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=1.[C:36]1([C:42]2[CH:47]=[C:46](B(O)O)[CH:45]=[C:44]([C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)[CH:43]=2)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(C)C=CC=CC=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.C(O)C>[C:36]1([C:42]2[CH:47]=[C:46]([C:18]3[C:19]4[C:24]([C:11]([C:8]5[CH:9]=[C:10]6[C:5]([CH:4]=[CH:3][C:2]([C:26]7[CH:35]=[CH:34][C:33]8[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=8)[CH:27]=7)=[CH:1]6)=[CH:6][CH:7]=5)=[C:12]5[C:17]=3[CH:16]=[CH:15][CH:14]=[CH:13]5)=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH:45]=[C:44]([C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)[CH:43]=2)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Komponenten

8

Edukt 4

HCID 1140TolueneHCID 62657Potassium Phosphate, TribasicHCID 14739363(1~1~,2~1~:2~3~,3~1~-Terphenyl)-2~5~-ylboronic acidHCID 867013529-([2,2'-Binaphthalen]-7-yl)-10-bromoanthracene

Produkt 1

HCID 867013559-([1,1':3',1''-Terphenyl]-5'-yl)-10-([2,2'-binaphthalen]-7-yl)anthraceneAusbeute 41,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 75806TricyclohexylphosphineKatalysatorHCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

Under the nitrogen atmosphere, [9-([2,2′-binaphthalen]-7-yl)-10-bromoanthracene (2.0 g) as the tenth intermediate compound, [1,1′:3′,1″-terphenyl]-5′-ylboronic acid (1.0 g), Pd(dba)2 (0.03 g), tricyclohexyl phosphine (0.03 g), potassium phosphate (1.3 g), and a mixture solvent of toluene and ethanol (20 ml) (toluene/ethanol=4/1 (volume ratio)) were added to a flask and refluxed for 2 hours. Once the heating is completed, the reaction solution was cooled to room temperature. The reaction was terminated by adding water. The target compound was extracted with toluene. The solvent was distilled off under reduced pressure, and the obtained crude product was purified by silica gel column chromatography (solvent: toluene) and also by active carbon column chromatography (solvent: toluene) to give 9-([1,1′:3′,1″-terphenyl]-5′-yl)-10-([2,2′-binaphthalen]-7-yl)anthracene (1.0 g) as the target compound represented by Formula (1-162). The scheme is shown in the following “Reaction 17”.

Aufarbeitung

  1. temperaturerefluxed for 2 hours
  2. customThe reaction was terminated
  3. additionby adding water
  4. extractionThe target compound was extracted with toluene
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe obtained crude product
  7. customwas purified by silica gel column chromatography (solvent: toluene) and also by active carbon column chromatography (solvent: toluene)

Quellen und Nachweise

ORD-Eintrag
ord-6158255d007747f1a36dd87fc4b56f0b
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09070885B2

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