Potassium Carbonate → 9-Phenylanthracene

HRID 1639479Notes

Reaction equation

HRID 1639479 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.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(=O)([O-])[O-].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.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

8

Reactant 4

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

Product 1

HCID 117669-PhenylanthraceneYield 92%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

In a 200 mL three-neck flask, 6.4 g (25 mmol) of 9-bromoanthracene, 3.0 g (25 mmol) of phenylboronic acid, 0.76 g (2.5 mmol) of tri(ortho-tolyl)phosphine, 60 mL of 1,2-dimethoxyethane (DME), and 25 mL of a 2.0 M potassium carbonate aqueous solution were added. The mixture was degassed by being stirred under reduced pressure, and the atmosphere in the flask was replaced with nitrogen. To the mixture, 0.11 g (0.50 mmol) of palladium(II) acetate was added and stirred under a nitrogen stream at 80° C. for 3 hours. After a predetermined time, water was added to the mixture, and an aqueous layer was extracted with toluene. The obtained extracted solution and the organic layer were combined and washed with saturated saline, and the organic layer was dried with magnesium sulfate. The obtained mixture was subjected to suction filtration through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135), and alumina, and the filtrate was concentrated to give a solid. The obtained solid was recrystallized with toluene/methanol to give 5.8 g of white powder, which was the object of the synthesis, in a yield of 92%.

Workup

  1. customThe mixture was degassed
  2. stirringstirred under a nitrogen stream at 80° C. for 3 hours
  3. extractionan aqueous layer was extracted with toluene
  4. extractionThe obtained extracted solution
  5. washwashed with saturated saline
  6. dry with materialthe organic layer was dried with magnesium sulfate
  7. filtrationThe obtained mixture was subjected to suction filtration through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135), and alumina
  8. concentrationthe filtrate was concentrated
  9. customto give a solid
  10. customThe obtained solid was recrystallized with toluene/methanol

Sources & evidence

ORD record
ord-6045010d92cd48f798d800ee973fd3ea
Source dataset
uspto-grants-2012_02
Patent number
US08110122B2

Reaction notes

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