N-bromobutanimide → N-(4-Bromophenyl)-4-biphenylamine

Participants

Reaction Steps

(Biphenyl-4-yl)-phenylamine (35.0 g) and DMF (700 ml) were added and dissolved in a nitrogen-substituted reaction vessel, and N-bromosuccinimide (8.5 g) was added under ice-cooled conditions. The reaction temperature was raised to room temperature while adding N-bromosuccinimide (17.0 g) in two separate portions. After being stirred for 25.5 hours, the reaction solution was dropped to water (3,500 ml), and the precipitated solid was collected by filtration. Toluene (2,500 ml) was added to dissolve the solid, and the solid was dried over magnesium sulfate. After filtration, the filtrate was concentrated. The resulting concentrate was dispersed and washed by addition of n-hexane (500 ml), and dried overnight under reduced pressure to obtain a reddish solid of (biphenyl-4-yl)-(4-bromophenyl)amine (44.1 g; yield 95.4%).

Provenance & Evidence