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

HRID 578601Notes

Reaction equation

HRID 578601 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][CH:3]=1.[CH3:9][C:10]1([CH3:44])[C:34]2[C:14]([CH:15]=[C:16]3[CH:33]=[C:32]4[C:19]([C:20]5[C:25]([C:26]6[C:31]4=[CH:30][CH:29]=[CH:28][CH:27]=6)=[CH:24][CH:23]=[CH:22][CH:21]=5)=[CH:18][C:17]3=2)=[CH:13][C:12](B2OC(C)(C)C(C)(C)O2)=[CH:11]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>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([C:12]2[CH:13]=[C:14]3[C:34]([C:10]([CH3:44])([CH3:9])[CH:11]=2)=[C:17]2[C:16]([CH:33]=[C:32]4[C:19](=[CH:18]2)[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:25]=2[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:31]4=2)=[CH:15]3)=[CH:3][CH:4]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 78041,4-DibromobenzeneHCID 10340Sodium CarbonateHCID 8671831210,10-dimethyl-(10H-indeno[1,2-b]triphenylen-12-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 8672361912-(4-bromophenyl)-10,10-dimethyl-10H-indeno[2,1-b]triphenyleneYield 53%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 6.6 g (28 mmol) of 1,4-dibromobenzene, 15.1 (32 mmol) of 2-(10,10-dimethyl-10H-indeno[1,2-b]triphenylen-12-yl)-4,4,5,5-teramethyl-1,3,2-dioxaborolane, 0.32 g (0.28 mmol) of Tetrakis(triphenylphosphine)palladium, 22 ml of 2M Na2CO3, 60 ml of EtOH and 130 ml toluene was degassed and placed under nitrogen, and then heated at 90° C. for 12 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 and the residue was purified by column chromatography on silica (hexane-dichloromethane) to give product 7.4 g (53%) as a white solid.

Workup

  1. customwas degassed
  2. customthe reaction
  3. temperatureto cool to room temperature
  4. filtrationthe precipitated product was filtered off with suction
  5. customthe residue was purified by column chromatography on silica (hexane-dichloromethane)

Sources & evidence

ORD record
ord-f21de77e2534442eb4877e530f829d2f
Source dataset
uspto-grants-2015_05
Patent number
US09040174B2

Reaction notes

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