Toluene → 2-Phenylanthraquinone

HRID 1827620

Reaktionsgleichung

Reaktionsgleichung von HRID 1827620
Cl[C:2]1[CH:15]=[CH:14][C:13]2[C:12](=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[O:17])[C:4]=2[CH:3]=1.[C:18]1(B(O)O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[F-].[K+].C1(C)C=CC=CC=1>O1CCOCC1.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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>[C:18]1([C:2]2[CH:15]=[CH:14][C:13]3[C:12](=[O:16])[C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[C:5](=[O:17])[C:4]=3[CH:3]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Komponenten

8

Edukt 4

HCID 1140TolueneHCID 85532-ChloroanthraquinoneHCID 66827Phenylboronic AcidHCID 522689Potassium Fluoride

Produkt 1

HCID 3139952-PhenylanthraquinoneAusbeute 87,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 83681Tris(1,1-dimethylethyl)phosphineKatalysatorHCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Under an atmosphere of argon, 2-chloroanthraquinone (5.0 g, 21 mmole), phenylboronic acid (2.8 g, 23 mmole, 1.1 eq), tris(dibenzylideneacetone)dipalladium(0) (0.2 g, 0.22 mmole, 2% Pd) and potassium fluoride (4.4 g, 76 mmole, 3.3 eq) were suspended in anhydrous dioxane (30 ml). To the obtained suspension, a toluene solution of tri-t-butylphosphine (66%, 0.13 ml, 0.42 mmole, 1 eq) was added and the resultant mixture was stirred at 80° C. for 3 hours. The reaction mixture was filtered and washed with toluene (100 ml). The filtrate was washed with a saturated aqueous solution of sodium chloride (30 ml) and dried with magnesium sulfate. Then, the solvent was removed by distillation and a yellow solid was obtained. The obtained solid was washed with boiling ethanol (50 ml) and a yellow solid (5.2 g, 87%) was obtained. 1H-NMR (CDCl3, TMS) δ: 7.4 to 7.6 (3H, m), 7.6 to 7.9 (4H, m), 7.98 (1H, dd, J=8 Hz, 2 Hz), 8.2 to 8.4 (3H, m), 8.50 (1H, d, J=2 Hz)

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. washwashed with toluene (100 ml)
  3. washThe filtrate was washed with a saturated aqueous solution of sodium chloride (30 ml)
  4. dry with materialdried with magnesium sulfate
  5. customThen, the solvent was removed by distillation
  6. customa yellow solid was obtained
  7. washThe obtained solid was washed with boiling ethanol (50 ml)

Quellen und Nachweise

ORD-Eintrag
ord-e777ef001ce44e7bb3ddd378ce85e87f
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07053255B2

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