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

HRID 1852553Notes

Reaction equation

HRID 1852553 reaction equation
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

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-407f4f5a7d484032bff8792d06b3ccd0
Source dataset
uspto-grants-2015_02
Patent number
US08962160B2

Reaction notes

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