Ethanol → 10,10-dimethyl-12-(10-(naphthalen-2-yl)anthracen-9-yl)-10H-indeno[1,2-b]triphenylene

HRID 1775392

Reaction equation

HRID 1775392 reaction equation
Br[C:2]1[C:3]2[C:8]([C:9]([C:16]3[CH:25]=[CH:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH:17]=3)=[C:10]3[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.[CH3:26][C:27]1([CH3:61])[C:51]2[C:31]([CH:32]=[C:33]3[CH:50]=[C:49]4[C:36]([C:37]5[C:42]([C:43]6[C:48]4=[CH:47][CH:46]=[CH:45][CH:44]=6)=[CH:41][CH:40]=[CH:39][CH:38]=5)=[CH:35][C:34]3=2)=[CH:30][C:29](B2OC(C)(C)C(C)(C)O2)=[CH:28]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.C1(C)C=CC=CC=1>[CH3:61][C:27]1([CH3:26])[C:51]2[C:31]([CH:32]=[C:33]3[CH:50]=[C:49]4[C:36]([C:37]5[C:42]([C:43]6[C:48]4=[CH:47][CH:46]=[CH:45][CH:44]=6)=[CH:41][CH:40]=[CH:39][CH:38]=5)=[CH:35][C:34]3=2)=[CH:30][C:29]([C:2]2[C:3]3[C:8]([C:9]([C:16]4[CH:25]=[CH:24][C:23]5[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=5)[CH:17]=4)=[C:10]4[C:15]=2[CH:14]=[CH:13][CH:12]=[CH:11]4)=[CH:7][CH:6]=[CH:5][CH:4]=3)=[CH:28]1

Participants

7

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 161162639-Bromo-10-(naphthalen-2-yl)anthraceneHCID 8671831210,10-dimethyl-(10H-indeno[1,2-b]triphenylen-12-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 8671831310,10-dimethyl-12-(10-(naphthalen-2-yl)anthracen-9-yl)-10H-indeno[1,2-b]triphenyleneYield 53%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 6.6 g (17.2 mmol) of 9-bromo-10-(naphthalene-2-yl)anthracene, 8.1 g (17.2 mmol) of 2-(10,10-dimethyl-10H-indeno[1,2-b]triphenylen-12-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 0.2 g (0.172 mmol) of Tetrakis(triphenylphosphine)palladium, 13 ml of 2M Na2CO3, 30 ml of EtOH and 100 ml toluene was degassed and placed under nitrogen, and then heated at 90° C. for 24 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 5.9 g (yield 53%) of yellow product which was recrystallized from toluene. MS(m/z,FAB+): 646.4; 1H NMR (CDCl3, 400 MHz): chemical shift(ppm) 9.14 (s, 1H), 8.90 (d, J=7.80 Hz, 1H), 8.82 (d, J=7.92 Hz, 1H), 8.79 (s, 1H), 8.73 (d, J=7.88 Hz, 2H), 8.23 (d, J=7.72 Hz, 1H), 8.11 (d, J=8.24 Hz, 1H), 8.07˜8.02 (m, 2H), 7.96 (d, J=7.40 Hz, 1H), 7.89 (d, J=8.64 Hz, 2H), 7.78˜7.59 (m, 10H), 7.42˜7.33 (m, 4H), 7.20 (d, J=7.40 Hz, 1H), 1.76 (s, 6H).

Workup

  1. customwas degassed
  2. temperatureto cool to room temperature
  3. additionThan 500 ml MeOH was added
  4. filtrationthe precipitated product was filtered off with suction

Sources & evidence

ORD record
ord-0235cc6c3ca042f9894b2e2b788cf6ec
Source dataset
uspto-grants-2016_02
Patent number
US09260363B2

Linked notes

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