Diphenylamine → 4-Methoxytriphenylamine

Participants

Reaction Steps

According to the general procedure A described above, 4-chloroanisole (130 mg, 0.92 mmol) reacted with diphenylamine (169 mg, 1.00 mmol) at 80° C. for 12 h using 1 mol % of Pd(dba)2/Ph5FcP(t-Bu)2 catalyst and sodium tert-butoxide to give the title compound (270 mg, 99%) as a solid: 1H-NMR (300 MHz, CDCl3): δ 7.30 (app.t, 4H, J=7.5 and 8.1 Hz), 7.17 (app.t, 6H, J=8.4 and 9.0 Hz), 7.04 (app.t, 2H, J=7.2 and 6.9 Hz), 6.94 (d, 2H, J=9.0 Hz), 3.88 (s, 3H). 13C{1H}-NMR (100 MHz, CDCl3): δ 156.11, 148.13, 140.74, 129.04, 127.26, 122.84, 121.78, 114.71, 55.44. GC/MS(EI): m/z 275 (M+).

Provenance & Evidence