Toluene → 1,5-Diphenylnaphthalene

HRID 909964Notes

Reaction equation

HRID 909964 reaction equation
FC(F)(F)S(O[C:7]1[C:16]2[C:11](=[C:12](OS(C(F)(F)F)(=O)=O)[CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1)(=O)=O.[C:27]1(B(O)O)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[C:36]1(C)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=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.C(COC)OC>[C:27]1([C:7]2[C:16]3[C:11](=[C:12]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[CH:13]=[CH:14][CH:15]=3)[CH:10]=[CH:9][CH:8]=2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 149765711,5-Naphthalenebis(trifluoromethanesulfonate)

Product 1

HCID 534856461,5-DiphenylnaphthaleneYield 60%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

Under an argon gas atmosphere, 49.0 g (106.1 mmol) of 5-{[(trifluoromethyl) sulfonyl]oxy}naphthyl trifluoromethanesulfonate, 28.5 g (233.3 mmol) of phenylboronic acid, 4.90 g (4.24 mmol) of tetrakis(triphenylphosphine)palladium(0), 200 ml of toluene, 100 ml of dimethoxyethane and 320 ml of 2M sodium carbonate solution were mixed, and stirred for 24 hours at 90 degrees C. After the reaction in the mixture was over, the mixture experienced filtration, through which aqueous phase thereof was eliminated. After organic phase thereof was cleansed by water and dried with magnesium sulfate, the solvent was distilled away under reduced pressure. Residue thereof was refined by silica-gel column chromatography, such that 18.0 g of 1.5-diphenylnaphthalene was obtained with an yield of 60%.

Workup

  1. customAfter the reaction in the mixture
  2. filtrationfiltration
  3. dry with materialdried with magnesium sulfate
  4. distillationthe solvent was distilled away under reduced pressure
  5. customwas obtained with an yield of 60%

Sources & evidence

ORD record
ord-70a514ec449d442994e92d984500aa5b
Source dataset
uspto-grants-2011_09
Patent number
US08021574B2

Reaction notes

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