Ethanol → 10,10,10',10'-tetramethyl-10H,10'H-12,12'-biindeno[1,2-b]triphenylene

HRID 578605Notes

Reaction equation

HRID 578605 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:24]([C:25]([CH3:28])([CH3:27])[CH:26]=1)=[C:7]1[CH:8]=[C:9]3[C:22](=[CH:23][C:6]1=[CH:5]2)[C:21]1[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:15]1[C:10]3=[CH:11][CH:12]=[CH:13][CH:14]=1.[CH3:29][C:30]1([CH3:64])[C:54]2[C:34]([CH:35]=[C:36]3[CH:53]=[C:52]4[C:39]([C:40]5[C:45]([C:46]6[C:51]4=[CH:50][CH:49]=[CH:48][CH:47]=6)=[CH:44][CH:43]=[CH:42][CH:41]=5)=[CH:38][C:37]3=2)=[CH:33][C:32](B2OC(C)(C)C(C)(C)O2)=[CH:31]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>[CH3:27][C:25]1([CH3:28])[C:24]2[C:4]([CH:5]=[C:6]3[CH:23]=[C:22]4[C:9]([C:10]5[C:15]([C:16]6[C:21]4=[CH:20][CH:19]=[CH:18][CH:17]=6)=[CH:14][CH:13]=[CH:12][CH:11]=5)=[CH:8][C:7]3=2)=[CH:3][C:2]([C:32]2[CH:33]=[C:34]3[C:54]([C:30]([CH3:64])([CH3:29])[CH:31]=2)=[C:37]2[CH:38]=[C:39]4[C:52](=[CH:53][C:36]2=[CH:35]3)[C:51]2[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=2)[C:45]2[C:40]4=[CH:41][CH:42]=[CH:43][CH:44]=2)=[CH:26]1

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 8671831210,10-dimethyl-(10H-indeno[1,2-b]triphenylen-12-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 8672032712-bromo-10,10-dimethyl-10H-indeno[1,2-b]triphenylene

Product 1

HCID 8672032610,10,10',10'-tetramethyl-10H,10'H-12,12'-biindeno[1,2-b]triphenyleneYield 49%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4.2 g (10 mmol) of 12-bromo-10,10-dimethyl-10H-indeno[1,2-b]triphenylene, 5.2 g (11 mmol) of 2-(10,10-dimethyl-10H-indeno[1,2-b]triphenylen-12-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 0.12 g (0.1 mmol) of Tetrakis(triphenylphosphine)Palladium, 15 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 finishing the reaction, The mixture was allowed to cool to room temperature. Than 100 ml MeOH was added, while stirring and the precipitated product was filtered off with suction. To give 3.3 g (yield 49%) of yellow product which was recrystallized from chloroform. MS (m/z, EI): 686.7. 1H NMR (CDCl3, 400 MHz): δ 9.05 (s, 2H), 8.86 (d, J=7.88 Hz, 2H), 8.79 (d, J=7.76 Hz, 2H), 8.74 (s, 2H), 8.71 (d, J=7.84 Hz, 4H), 8.10 (d, J=7.64 Hz, 2H), 7.84 (s, 2H), 7.81 (d, J=7.80 Hz, 2H), 7.76˜7.67 (m, 8H), 1.77 (s, 12H).

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-677457d037fe4ad89952f5b097f878ee
Source dataset
uspto-grants-2015_05
Patent number
US09040174B2

Reaction notes

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