1,3-Dibromobenzene → 3-Bromo-N,N-diphenylaniline

Participants

Reaction Steps

Diphenylamine (9 g, 53.3 mmol), and 1,3-dibromobenzene (25 g, 106.8 mmol) were mixed in toluene (500 mL). The solution was bubbled nitrogen while stirring for 15 min. Pd(OAc)2 (0.18 g, 0.8 mmol), triphenylphosphine (0.84 g, 3.2 mmol) and tBuONa (7.7 g, 80.2 mmol) were added in sequence. The mixture was heated to reflux overnight under nitrogen. After cooling, the reaction mixture was filtered through Celite®/silica pad and the solvent was then evaporated. The residue was purified by column using hexane as eluent to obtain 13.5 g (60%) of 3-bromo-N,N-diphenylaniline.

Provenance & Evidence