Reaktion #11842

Reaktionsgleichung

4,4′-Dibromo-2-amino-1,1′-biphenyl

4-iodoanisole

potassium carbonate

nitrobenzene

→

off-white crystals

4,4′-Dibromo-2-Bis(4-Methoxyphenyl)Amino-1,1′-Biphenyl

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturat gentle reflux for 15 hours
2. 2
   SonstigeThe dark reaction mixture
3. 3
   Extraktionextracted with 200 ml of toluene
4. 4
   SonstigeThe toluene solution was evaporated
5. 5
   SonstigeThe dark residue obtained
6. 6
   Sonstigechromatographed on a silica gel column
7. 7
   workup.ADDITIONThe portions containing the product
8. 8
   Sonstigewere collected
9. 9
   Sonstigeevaporated
10. 10
    SonstigeThe residue was recrystallized twice from hexane/toluene (300 ml/60 ml)

Vorschrift

4,4′-Dibromo-2-amino-1,1′-biphenyl (16.35 g, 0.05 mol), 4-iodoanisole (28 g, 0.12 mol), potassium carbonate (−325 mesh fine powder, 16.6 g, 0.12 mole), copper dust (−150 mesh,1.0 g), and nitrobenzene (20 ml) were charged into a flask and stirred at gentle reflux for 15 hours. The dark reaction mixture was cooled to room temperature and extracted with 200 ml of toluene. The toluene solution was evaporated. The dark residue obtained was then mixed with 10 ml of toluene and chromatographed on a silica gel column using hexane and hexane/ethyl acetate (20:1) eluant. The portions containing the product were collected and evaporated. The residue was recrystallized twice from hexane/toluene (300 ml/60 ml) to yield 7.4 grams of off-white crystals of the desired monomer. 1H NMR (CDCl3): δ=6.8–7.5 (15H, multiple peaks); 3.78 (6H).

Quelle