Potassium Carbonate → 9-Phenylanthracene

HRID 1160982Notes

Reaction equation

HRID 1160982 reaction equation
Br[C:2]1[C:3]2[C:8]([CH:9]=[C:10]3[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.[C:16]1([BrH](O)(=O)=O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>CC([O-])=O.CC([O-])=O.[Pd+2].COCCOC>[C:16]1([C:2]2[C:3]3[C:8]([CH:9]=[C:10]4[C:15]=2[CH:14]=[CH:13][CH:12]=[CH:11]4)=[CH:7][CH:6]=[CH:5][CH:4]=3)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 740629-BromoanthraceneHCID 80271Tri-o-tolylphosphine

Product 1

HCID 117669-PhenylanthraceneYield 85%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

5.4 g (21.1 mmol) of 9-bromoanthracene, 2.6 g (21.1 mmol) of phenylbromic acid, 60 mg (0.21 mmol) of Pd(OAc)2, 10 ml (20 mmol) of a 2 mol/l potassium carbonate (K2CO3) aqueous solution, 263 mg (0.84 mmol) of tri(orthotolyl)phosphine (P(o-tolyl)3), and 20 ml of 1,2-dimethoxyethane (abbrev.: DME) were mixed, and stirred for 9 hours at 80° C. After the reaction, the solid extracted was recovered by suction filtration. Then it was dissolved in toluene and filtered through Florisil, Celite, and alumina. After the filtrate was washed by water and a saturated saline solution, it was dried with magnesium sulfate. After natural filtration, the filtrate was concentrated, and the target substance of 9-phenylanthracene was obtained in a light brown solid form, weighing 21.5 g in a yield of 85% (synthesis scheme (j-3)).

Workup

  1. customAfter the reaction
  2. extractionthe solid extracted
  3. filtrationwas recovered by suction filtration
  4. dissolutionThen it was dissolved in toluene
  5. filtrationfiltered through Florisil, Celite, and alumina
  6. washAfter the filtrate was washed by water
  7. dry with materiala saturated saline solution, it was dried with magnesium sulfate
  8. filtrationAfter natural filtration
  9. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-9b366106c1254cac8fbfdef915bc4116
Source dataset
uspto-grants-2010_10
Patent number
US07816668B2

Reaction notes

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