Quinone → 6,13-Pentacenequinone

HRID 1943011

Reaktionsgleichung

Reaktionsgleichung von HRID 1943011
Br[CH:2](Br)[C:3]1[C:4]([CH:9](Br)Br)=[CH:5][CH:6]=[CH:7][CH:8]=1.[C:13]1(=[O:20])[CH:18]=[CH:17][C:16](=[O:19])[CH:15]=[CH:14]1.[I-].[Na+]>CN(C=O)C>[CH:5]1[C:4]2[C:3](=[CH:2][C:18]3[C:13](=[O:20])[C:14]4[C:15]([C:16](=[O:19])[C:17]=3[CH:9]=2)=[CH:9][C:4]2[C:3](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:2]=4)[CH:8]=[CH:7][CH:6]=1

Komponenten

5

Edukt 3

HCID 4650QuinoneHCID 5238Sodium IodideHCID 832341,2-Bis(dibromomethyl)benzene

Produkt 1

HCID 764156,13-PentacenequinoneAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a clear solution of α,α,α′,α′-tetrabromo-o-xylene (30.5 g, 0.073 mol) in DMF (100 mL) was added benzoquinone (3.125 g, 0.03 mol) and sodium iodide (27.25 g, 0.18 mol). The resulting brown suspension was heated and stirred at 120° C. overnight. After cooling to RT, the yellow solids were filtered via vacuum filtration. The yellow solids were washed with water, saturated sodium bisulfite solution and dried to yield the product (8.1 g, 91%). 1H NMR (500 MHz, CDCl3): δ 8.96 (s, 4H), 8.14 (m, 4H), 7.72 (m, 4H). 13C NMR (125.68 MHz, CDCl3): δ 183.2, 135.47, 130.80, 130.30, 129.98, 129.66. m/z: 308 [W].

Aufarbeitung

  1. temperatureThe resulting brown suspension was heated
  2. temperatureAfter cooling to RT
  3. filtrationthe yellow solids were filtered via vacuum filtration
  4. washThe yellow solids were washed with water, saturated sodium bisulfite solution
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-037ca8fc57134728ae335a2b700062df
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08389744B1

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