Ethanol → 10,10-dimethyl-12-(3-(pyren-1-yl)phenyl)-10H-indeno[1,2-b]triphenylene

HRID 1852553Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1852553
Br[C:2]1[CH:3]=[C:4]([C:8]2[C:21]3[C:22]4=[C:23]5[C:18](=[CH:19][CH:20]=3)[CH:17]=[CH:16][CH:15]=[C:14]5[CH:13]=[CH:12][C:11]4=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:24][C:25]1([CH3:59])[C:49]2[C:29]([CH:30]=[C:31]3[CH:48]=[C:47]4[C:34]([C:35]5[C:40]([C:41]6[C:46]4=[CH:45][CH:44]=[CH:43][CH:42]=6)=[CH:39][CH:38]=[CH:37][CH:36]=5)=[CH:33][C:32]3=2)=[CH:28][C:27](B2OC(C)(C)C(C)(C)O2)=[CH:26]1.C([O-])([O-])=O.[Na+].[Na+].CCO>CO.C1(C)C=CC=CC=1>[CH3:59][C:25]1([CH3:24])[C:49]2[C:29]([CH:30]=[C:31]3[C:32]=2[CH:33]=[C:34]2[C:47]([C:46]4[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=4[C:40]4[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=42)=[CH:48]3)=[CH:28][C:27]([C:6]2[CH:7]=[CH:2][CH:3]=[C:4]([C:8]3[C:21]4[C:22]5=[C:23]6[C:18](=[CH:19][CH:20]=4)[CH:17]=[CH:16][CH:15]=[C:14]6[CH:13]=[CH:12][C:11]5=[CH:10][CH:9]=3)[CH:5]=2)=[CH:26]1

Komponenten

7

Edukt 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 578361411-(3-Bromophenyl)pyreneHCID 8671831210,10-dimethyl-(10H-indeno[1,2-b]triphenylen-12-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Produkt 1

HCID 8671831410,10-dimethyl-12-(3-(pyren-1-yl)phenyl)-10H-indeno[1,2-b]triphenyleneAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 5 g (14 mmol) of 1-(3-bromophenyl)pyrene, 7.53 g (16 mmol) of 2-(10,10-dimethyl-10H-indeno[1,2-b]triphenylen-12-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 0.16 g (0.14 mmol) of tetrakis(triphenyl phosphine)palladium, 11 ml of 2M Na2CO3, 30 ml of EtOH and 65 ml toluene was degassed and placed under nitrogen, and then heated at 90° C. for 4 h. After finishing the reaction, the mixture was allowed to cool to room temperature. Than 500 ml MeOH was added, while stirring and the precipitated product was filtered off with suction to give 4.95 g (yield 57%) of yellow product which was recrystallized from toluene. MS(m/z, FAB+): 620.1; 1H NMR (CDCl3, 400 MHz): chemical shift (ppm) 9.05 (s, 1H), 8.46˜8.41 (m, 2H), 8.40 (s, 1H), 8.06˜7.84 (m, 9H), 7.74 (d, J=8.00 Hz, 1H), 7.69˜7.59 (m, 4H), 7.54˜7.39 (m, 5H), 7.31˜7.16 (m, 3H), 1.82 (s, 6H).

Aufarbeitung

  1. customwas degassed
  2. customthe reaction
  3. temperatureto cool to room temperature
  4. filtrationthe precipitated product was filtered off with suction

Quellen und Nachweise

ORD-Eintrag
ord-407f4f5a7d484032bff8792d06b3ccd0
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08962160B2

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