2-Bromotoluene → N-(2-tolyl)diphenylamine

Participants

Reaction Steps

The above general procedure was followed using 2-bromotoluene (188 mg, 1.10 mmol) and diphenylamine (169 mg, 1.00 mmol) with 1 mol % Pd(dba)2 and 0.8 mol % tri-t-butylphosphine in 1.5 mL of toluene. After four hours, the reaction mixture was adsorbed onto silica gel and chromatographed with 2.5% ethyl acetate/hexanes to give 247 mg (95%) of N-(2-tolyl)diphenylamine as a colorless oil that crystallized to a white solid. 1H NMR (500 MHz, C6D6) δ 7.05-6.96 (m, 12 H), 6.78 (tt, J=7.25, 1.30 Hz, 2H), 1.99 (s, 3H). 13C NMR (125 MHz, C6D6) δ 148.0, 146.0, 136.6, 132.0, 129.9, 129.4, 127.7, 126.1, 122.0, 121.8, 18.7.

Provenance & Evidence