Sodium Carbonate → 2-(2-Anthryl)triphenylene

HRID 467420Notes

Reaction equation

HRID 467420 reaction equation
[CH:1]1[C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][C:2]=1B(O)O.Br[C:23]1[CH:36]=[CH:35][C:34]2[C:25](=[CH:26][C:27]3[C:32]([CH:33]=2)=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+]>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.COCCOC>[CH:24]1[C:25]2[C:34](=[CH:33][C:32]3[C:27]([CH:26]=2)=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:35]=[CH:36][C:23]=1[C:14]1[CH:15]=[CH:16][C:17]2[C:18]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:12]=2[CH:13]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 123460992-BromoanthraceneHCID 59805119Triphenylen-2-ylboronic acid

Product 1

HCID 595830242-(2-Anthryl)triphenyleneYield 75.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

Under an argon atmosphere, 7.79 g of triphenylene-2-boronic acid piconal ester, 5.14 g of 2-bromoanthracene, 0.462 g of tetrakis(triphenylphosphine)palladium (0), 30 mL of 1,2-dimethoxyethane and 15 mL of a 2M sodium carbonate aqueous solution were placed in a flask, and refluxed with stirring for 8 hours. After cooling to room temperature, deposited crystals were collected by filtration. The resulting solid was subjected to repeated recrystallization with toluene-hexane and washing to obtain 6.07 g (yield: 75%) of 2-(2-anthryl)triphenylene.

Workup

  1. temperaturerefluxed
  2. filtrationwere collected by filtration
  3. customrecrystallization with toluene-hexane
  4. washwashing

Sources & evidence

ORD record
ord-1ef257dff279423a839b8233ec12df4c
Source dataset
uspto-grants-2014_01
Patent number
US08623520B2

Reaction notes

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