Potassium Carbonate → 9-Phenylanthracene

HRID 2117824Notes

Reaction equation

HRID 2117824 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(B(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.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 66827Phenylboronic AcidHCID 740629-Bromoanthracene

Product 1

HCID 117669-PhenylanthraceneYield 400.7%

Reagents, catalysts & solvents 2

HCID 80271Tri-o-tolylphosphineCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

5.4 g (21.1 mmol) of 9-bromoanthracene, 2.6 g (21.1 mmol) of phenylboronic acid, 60 mg (0.21 mmol) of palladium acetate(II) (Pd(OAc)2), 10 mL (20 mmol) of an aqueous potassium carbonate (K2CO3) solution (2 mol/L), 263 mg (0.84 mmol) of tri(o-tolyl)phosphine (P(o-tolyl)3), and 20 mL of 1,2-dimethoxyethane (abbr.: DME) were mixed and stirred for 9 hours at 80° C. After the reaction, the precipitated solid was recovered by suction filtration, dissolved into toluene, and filtered through florisil, Celite®, and alumina. The filtrate was washed with a saturated aqueous sodium chloride solution and then dried with magnesium sulfate. After natural filtration, the filtrate was concentrated, thereby obtaining 21.5 g of objective 9-phenylanthracene as a light-brown solid with a yield of 85. %.

Workup

  1. customAfter the reaction
  2. filtrationthe precipitated solid was recovered by suction filtration
  3. dissolutiondissolved into toluene
  4. filtrationfiltered through florisil, Celite®, and alumina
  5. washThe filtrate was washed with a saturated aqueous sodium chloride solution
  6. dry with materialdried with magnesium sulfate
  7. filtrationAfter natural filtration
  8. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-fcff9ea6a58c4acd8d5f7589fef2810a
Source dataset
uspto-grants-2008_10
Patent number
US07442803B2

Reaction notes

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