Ethanol → 10,10-dimethyl-12-(4-(pyren-1-yl)phenyl)-10H-indeno[1,2-b]triphenylene

HRID 1775388Notes

Reaction equation

HRID 1775388 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([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:4][CH:3]=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>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.CO.C1(C)C=CC=CC=1>[CH3:59][C:25]1([CH3:24])[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]([C:2]2[CH:3]=[CH:4][C:5]([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:6][CH:7]=2)=[CH:26]1

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 221380391-(4-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 8671830910,10-dimethyl-12-(4-(pyren-1-yl)phenyl)-10H-indeno[1,2-b]triphenyleneYield 57%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 5 g (14 mmol) of 1-(4-bromophenyl)pyrene, of 7.53 (16 mmol) 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(triphenylphosphine)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 12 h. After the reaction finish, 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+): 620.2; 1H NMR (CDCl3, 400 MHz): chemical shift(ppm) 9.06 (s, 1H), 8.86 (d, J=8.00 Hz, 1H), 8.80 (d, J=8.00 Hz, 1H), 8.75 (s, 1H), 8.71 (d, J=8.00 Hz, 2H), 8.33˜8.27 (m, 2H), 8.22˜8.20 (m, 2H), 8.14˜8.05 (m, 6H), 7.94 (d, J=8.00 Hz, 2H), 7.89 (s, 1H), 7.85˜7.69 (m, 7H), 1.77 (s, 6H).

Workup

  1. temperatureto cool to room temperature
  2. filtrationthe precipitated product was filtered off with suction

Sources & evidence

ORD record
ord-74094cf1745040d383c9f9e1048d6de7
Source dataset
uspto-grants-2016_02
Patent number
US09260363B2

Reaction notes

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