N-Methylaniline → HCID 10219937, compound

Participants

Reaction Steps

The above general procedure was followed using 4-bromobenzonitrile (187 mg, 1.00 mmol) and N-methylaniline (107 mg, 1.00 mmol) with 1 mol % Pd(dba)2 and 0.8 mol % tri-t-butylphosphine in 1.0 mL of toluene. After 6 hours, the reaction mixture was adsorbed onto silica gel and chromatographed with 10% ethyl acetate/hexanes to give 201 mg (97%) of N-(4-cyanophenyl)-N-methylaniline. 1H NMR (500 MHz, CDCl3) δ 7.45-7.42 (m, 4H), 7.27 (t, J=7.5 Hz, 1H), 7.21 (d, J=8.3 Hz, 2H), 6.73 (d, J=9.0 Hz, 2H), 3.36 (s, 3H). 13C NMR (125 MHz, CDCl3) δ 152.0, 146.8, 133.1, 130.1, 126.4, 126.2, 120.2, 114.0, 99.4, 40.1.

Provenance & Evidence