p-Toluenesulfonic acid → 4,4'-Dibromotriphenylamine

HRID 571023

Reaktionsgleichung

Reaktionsgleichung von HRID 571023
[CH:1]1[C:6]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][CH:9]=2)=[CH:5][CH:4]=[C:3]([Br:15])[CH:2]=1.[C:16]1(=O)[CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH:16]1[CH:21]=[CH:20][C:19]([N:7]([C:8]2[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][CH:9]=2)[C:6]2[CH:1]=[CH:2][C:3]([Br:15])=[CH:4][CH:5]=2)=[CH:18][CH:17]=1

Komponenten

5

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 125111,4-CyclohexanedioneHCID 629950Bis(4-bromophenyl)amine

Produkt 1

HCID 135947074,4'-DibromotriphenylamineAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

A mixture of 4,4′-dibromodiphenylamine (7.3 g. 22 mmol), cyclohexane-1,4-dione (2.5 g., 23.3 mole), para-toluenesulfonic acid (0.1 g.), and toluene (100 mL) was kept at reflux with a Dean-Stark 15 phase separator containing 4A molecular sieves. After 18 hours at reflux, the reaction was diluted with toluene, and the toluene solution was washed with water, dried, and concentrated. The residue was dissolved in hexanes, and the hexanes solution was then passed through a column of silica gel to afford 4,4′-dibromotriphenylamine as a colorless glass, 5.04 g., 67% yield. Mass Spec (m/z): 401, 403, 405 (M+).

Aufarbeitung

  1. temperatureat reflux with a Dean-Stark 15 phase separator
  2. temperatureAfter 18 hours at reflux
  3. washthe toluene solution was washed with water
  4. customdried
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-bdf96a7afd554b108fcf9d56789309d2
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09024037B1

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