Water → 4,4'-Dibromotriphenylamine

HRID 480997

Reaktionsgleichung

Reaktionsgleichung von HRID 480997
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[C:16]1(=O)[CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[CH:16]1[CH:21]=[CH:20][C:19]([N:8]([C:9]2[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][CH:10]=2)[C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=2)=[CH:18][CH:17]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 125111,4-CyclohexanedioneHCID 521998p-Toluenesulfonic acid monohydrateHCID 629950Bis(4-bromophenyl)amine

Produkt 1

HCID 135947074,4'-DibromotriphenylamineAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

The preparation was carried out analogously to K. Haga et al, Bull. Chem. Soc. Jpn., 1986, 59, 803-7: 3.10 g (10.4 mmol) of bis(4-bromophenyl)amine (J. Berthelot et al, Can. J. Chem., 1989, 67, 2061), 1.28 g of cyclohexane-1,4-dione (11.4 mmol) and 2.17g (11.4 mmol) of p-toluenesulfonic acid hydrate were heated in 50 ml of toluene on a water separator. After a reaction time of 12 hours, the solvent was removed and the product was purified by column chromatography (hexane/ethyl acetate 4:1). 3.82 g (9.46 mmol, 91%) of 4,4′-dibromotriphenylamine were obtained as a viscous oil.

Aufarbeitung

  1. customAfter a reaction time of 12 hours, the solvent was removed
  2. customthe product was purified by column chromatography (hexane/ethyl acetate 4:1)

Quellen und Nachweise

ORD-Eintrag
ord-b8f7a43c29f643acb478df797266f201
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06653438B1

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