Potassium Carbonate → 9-Phenylanthracene

HRID 80288

Reaction equation

HRID 80288 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>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.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

7

Reactant 4

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 740629-BromoanthraceneHCID 80271Tri-o-tolylphosphine

Product 1

HCID 117669-PhenylanthraceneYield 85%

Reagents, catalysts & solvents 2

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

Procedure

Into a 200 mL three-neck flask were put 5.4 g (21 mmol) of 9-bromoanthracene, 2.6 g (21 mmol) of phenylboronic acid, 60 mg (0.2 mmol) of palladium(II) acetate (abbr.: Pd(OAc)2), 10 mL (20 mmol) of potassium carbonate solution (2.0 mol/L), 260 mg (0.8 mmol) of tris(o-tolyl)phosphine (abbr.: P(o-tolyl)3), and 20 mL of ethylene glycol dimethyl ether, and then the mixture was stirred at 80° C. under a nitrogen stream for 9 hours. After the stirring, a precipitated solid was collected by suction filtration, dissolved in toluene, and filtered through Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135), Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), and alumina. The obtained filtrate was washed with water and saturated saline, followed by drying with magnesium sulfate. This suspending solution was gravity filtered and the obtained filtrate was concentrated, whereby 22 g of a light-brown solid of 9-phenylanthracene, which was the object of the synthesis, was obtained in a yield of 85% (synthesis scheme (X-1)).

Workup

  1. customInto a 200 mL three-neck flask were put
  2. filtrationAfter the stirring, a precipitated solid was collected by suction filtration
  3. dissolutiondissolved in toluene
  4. filtrationfiltered through Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135), Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), and alumina
  5. washThe obtained filtrate was washed with water and saturated saline
  6. dry with materialby drying with magnesium sulfate
  7. filtrationfiltered
  8. concentrationthe obtained filtrate was concentrated
  9. customthe object of the synthesis
  10. customwas obtained in a yield of 85% (synthesis scheme (X-1))

Sources & evidence

ORD record
ord-2b8e723bb9f346eb9c93e8870d62acd4
Source dataset
uspto-grants-2014_09
Patent number
US08845926B2

Linked notes

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