4,4'-Dimethoxydiphenylamine → 4-Methoxy-N,N-bis(4-methoxyphenyl)benzenamine

Participants

Reaction Steps

The above general procedure was followed using 4-bromoanisole (187 mg, 1.00 mmol) and di(4-methoxyphenyl)amine (229 mg, 1.00 mmol) with 1 mol % Pd(dba)2 and 0.8 mol % tri-t-butylphosphine in 1.5 mL of toluene. After one hour, the reaction mixture was adsorbed onto silica gel and chromatographed with 5% ethyl acetate/hexanes to give 321 mg (96%) of tri(4-methoxyphenyl)amine as a white solid. 1H NMR (500 MHz, C6D6) δ 7.08 (d, J=10 Hz, 6 H), 6.73 (d, J=10 Hz, 6H), 3.31 (s, 9H). 13C NMR (125 MHz, C6D6) δ 155.7, 142.6, 125.3, 115.0, 55.0.

Provenance & Evidence