Potassium Carbonate → 9-Phenylanthracene

HRID 1174435Notes

Reaction equation

HRID 1174435 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+].CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].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 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 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 Pd(OAc)2 (0), 10 mL (20 mmol) of an K2CO3 aqueous solution of 2M, 263 mg (0.84 mmol) of P(o-tolyl)3, and 20 mL of 1,2-dimethoxyethane (abbreviation: DME) are mixed, and then stirred for 9 hours at 80° C. After reaction, a precipitated solid was collected by suction filtration. Subsequently, the solid was dissolved in toluene and then filtered through Florisil®, celite, and alumina. After a filtrate was washed with water and saturated saline, it was dried with magnesium sulfate. After natural filtration, when the filtrate is condensed, 21.5 g of 9-phenylanthracene which is a target substance was obtained as a light brown solid at a yield of 85% (Synthesis Scheme (f-1)).

Workup

  1. customAfter reaction
  2. filtrationa precipitated solid was collected by suction filtration
  3. dissolutionSubsequently, the solid was dissolved in toluene
  4. filtrationfiltered through Florisil®, celite, and alumina
  5. washAfter a filtrate was washed with water and saturated saline, it
  6. dry with materialwas dried with magnesium sulfate
  7. filtrationAfter natural filtration, when the filtrate
  8. customcondensed, 21.5 g of 9-phenylanthracene which
  9. customwas obtained as a light brown solid at a yield of 85% (Synthesis Scheme (f-1))

Sources & evidence

ORD record
ord-2a9b99bba1e147aba9bccef4f0dd8843
Source dataset
uspto-grants-2010_11
Patent number
US07838128B2

Reaction notes

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