Potassium Phosphate, Tribasic → 9-(4-Methylnaphth-1-yl)anthracene

HRID 1190232Notes

Reaction equation

HRID 1190232 reaction equation
C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.[CH3:23][C:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27](B(O)O)=[CH:26][CH:25]=1.Br[C:38]1[C:39]2[C:44]([CH:45]=[C:46]3[C:51]=1[CH:50]=[CH:49][CH:48]=[CH:47]3)=[CH:43][CH:42]=[CH:41][CH:40]=2.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C1(C)C=CC=CC=1>[CH3:23][C:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27]([C:38]2[C:51]3[C:46]([CH:45]=[C:44]4[C:39]=2[CH:40]=[CH:41][CH:42]=[CH:43]4)=[CH:47][CH:48]=[CH:49][CH:50]=3)=[CH:26][CH:25]=1

Participants

9

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 740629-BromoanthraceneHCID 80271Tri-o-tolylphosphineHCID 27735114-Methyl-1-naphthaleneboronic acid

Product 1

HCID 577025649-(4-Methylnaphth-1-yl)anthracene

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Procedure

3.6 g (11.7 mmol) of tri-o-tolylphosphine and then 437 mg (1.9 mmol) of palladium(II) acetate are added with vigorous stirring to a suspension of 93.0 g (500 mmol) of 4-methylnaphthalene-1-boronic acid, 100.0 g (389 mmol) of 9-bromoanthracene, 212.3 g (1 mol) of tripotassium phosphate in a mixture of 400 ml of dioxane, 600 ml of toluene and 1000 ml of water, and the mixture is refluxed for 16 h. After the reaction mixture has been cooled, the organic phase is separated off and washed three times with 500 ml of water. The organic phase is subsequently filtered through silica gel and evaporated to dryness. The oil which remains is taken up in 1000 ml of ethanol and dissolved under reflux. After cooling, the colourless solid is filtered off with suction, again washed by stirring with 1000 ml of ethanol and finally dried under reduced pressure. Yield: 103.0 g (83.1% of theory), about 96% according to 1H-NMR.

Workup

  1. temperaturethe mixture is refluxed for 16 h
  2. temperatureAfter the reaction mixture has been cooled
  3. customthe organic phase is separated off
  4. washwashed three times with 500 ml of water
  5. filtrationThe organic phase is subsequently filtered through silica gel
  6. customevaporated to dryness
  7. dissolutiondissolved
  8. temperatureunder reflux
  9. temperatureAfter cooling
  10. filtrationthe colourless solid is filtered off with suction
  11. washagain washed
  12. customfinally dried under reduced pressure

Sources & evidence

ORD record
ord-d3e7195fd1e04e5a961bd3f9a5a4a3f4
Source dataset
uspto-grants-2014_03
Patent number
US08674141B2

Reaction notes

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