1,2-Dibromobenzene → 4-Bromotriphenylamine

Participants

Reaction Steps

In a two-neck round bottom flask, diphenylamine (50 g, 0.30 mol), dibromobenzene (104 g, 0.44 mol), BINAP[2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl] (7.4 g, 4% mol), Pd(OAc)2[Palladium(II)acetate] (2.0 g, 3% mol), and NaOtBu[Sodium tert-butoxide] (42.6 g, 0.44 mol) are dissolved in toluene (400 mL), and then are maintained for 24 hours by reflux. On completion of the reaction, the flask having the resultant solution is cooled, and then toluene, a solvent of the reaction, is removed from the resultant solution. After that, the resultant solution having no toluene reacts on methylene-chloride and water, and then methylene-chloride is removed therefrom, and is performed by silica gel column chromatography with a solvent of methylene-chloride and hexane at a ratio of 3 to 1. After that, the solvent is removed from the resultant solution of completing silica gel column chromatography, and is recrystallized and filtered with methylene-chloride and petroleum ether, thereby obtaining a white solid, (4-bromo-phenyl)-diphenyl-amine (36.5 g, 40%).

Provenance & Evidence