Potassium Carbonate → 9-Phenylanthracene

HRID 537591

Reaktionsgleichung

Reaktionsgleichung von HRID 537591
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

Komponenten

7

Edukt 4

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

Produkt 1

HCID 117669-PhenylanthraceneAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

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(II) acetate (abbreviation: Pd(OAc)2), 10 mL (20 mmol) of a potassium carbonate aqueous solution (2 mol/L), 263 mg (0.84 mmol) of tris(ortho-tolyl)phosphine (abbreviation: P(o-tolyl)3), and 20 mL of 1,2-dimethoxyethane (abbreviation: DME) were put in a 200 mL three neck flask, and then stirred for nine hours at 80° C. in nitrogen stream. 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 the mixture was subjected to natural filtration, when the filtrate was concentrated, 21.5 g of 9-phenylanthracene which was a target substance was obtained as a light brown solid at a yield of 85% (Synthesis scheme (b-1)).

Aufarbeitung

  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 the mixture was subjected to natural filtration, when the filtrate
  8. concentrationwas concentrated
  9. customwas obtained as a light brown solid at a yield of 85% (Synthesis scheme (b-1))

Quellen und Nachweise

ORD-Eintrag
ord-4e389874e59f47cf8a297b6f7d703899
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08860019B2

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