Sodium Carbonate → 5-(2-Anthryl)benzo[c]phenanthrene

HRID 1890213Notes

Reaction equation

HRID 1890213 reaction equation
[CH:1]1[C:18]2[C:17]3[C:16]4[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=4[CH:10]=[CH:9][C:8]=3[CH:7]=[C:6](B(O)O)[C:5]=2[CH:4]=[CH:3][CH:2]=1.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:10]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=2[C:17]2[C:18]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=3[CH:6]=[CH:7][C:8]=2[CH:9]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 123460992-BromoanthraceneHCID 59622711HCID 59622711, compound

Product 1

HCID 596227335-(2-Anthryl)benzo[c]phenanthreneYield 75.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

Under an argon atmosphere, 5.98 g of benzo[c]phenanthrene-5-boronic acid, 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 aqueous solution of sodium carbonate was charged, and the mixture was refluxed with stirring for 8 hours. After cooling to room temperature, deposited crystals were separated by filtration. The resulting solids were recrystallized with toluene-hexane and washed repeatedly, whereby 6.07 g (yield: 75%) of 5-(2-anthryl)benzo[c]phenanthrene was obtained.

Workup

  1. temperaturethe mixture was refluxed
  2. customwere separated by filtration
  3. customThe resulting solids were recrystallized with toluene-hexane
  4. washwashed repeatedly

Sources & evidence

ORD record
ord-922669b528694752a2f06aaff6dc3480
Source dataset
uspto-grants-2013_08
Patent number
US08507106B2

Reaction notes

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