Potassium Iodide → 2-Bromo-9,10-diphenylanthracene

HRID 1177819Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1177819
[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[C:12]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)(O)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)(O)[C:4]=2[CH:3]=1.[I-].[K+].O.[PH2](=O)[O-].[Na+].[PH2](=O)O>C(O)(=O)C>[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[C:5]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:6]3[C:11]([C:12]=2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:3]=1

Komponenten

6

Edukt 4

HCID 4875Potassium IodideHCID 4124402Phosphinic AcidHCID 231602182-Bromo-9,10-diphenyl-9,10-dihydroanthracene-9,10-diolHCID 178418950HCID 178418950, Verbindung

Produkt 1

HCID 222471632-Bromo-9,10-diphenylanthraceneAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

7.55 g (16.95 mmol) of the obtained 2-bromo-9,10-diphenyl-9,10-dihydroanthracene-9,10-diol, 5.06 g (30.51 mmol) of potassium iodide, 9.70 g (91.52 mmol) of sodium phosphinate monohydrate, and 50 mL of glacial acetic acid were put into a 500 mL three-neck flask, and the mixture was heated at 120° C. for 2 hours. Thereafter, 30 mL of 50% phosphinic acid was added to the mixture, and the mixture was stirred for 1 hour at 120° C. After the reaction, the mixture was washed with water, and the aqueous layer was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and concentrated. The residue was dissolved in toluene, and the solution was filtered through celite, Florisil, and then alumina. The filtrate was concentrated, and the residue was recrystallized with chloroform and hexane, giving 5.1 g of 2-bromo-9,10-diphenylanthracene as a light yellow solid in 74% yield.

Aufarbeitung

  1. customAfter the reaction
  2. washthe mixture was washed with water
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe residue was dissolved in toluene
  8. filtrationthe solution was filtered through celite, Florisil
  9. concentrationThe filtrate was concentrated
  10. customthe residue was recrystallized with chloroform and hexane

Quellen und Nachweise

ORD-Eintrag
ord-44b959f434fc42579955fdecc8a3fd34
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07842945B2

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