Nitrobenzene → 4,4'-Dibromo-2-bis(4-methoxyphenyl)amino-1,1'-biphenyl

Participants

Reaction Steps

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 (15 H, multiple peaks); 3.78 (6 H).

Provenance & Evidence