2-Bromotoluene → HCID 9794453, compound

Participants

Reaction Steps

The above general procedure was followed using 2-bromotoluene (171 mg, 1.00 mmol) and dibutylamine (129 mg, 1.00 mmol) with 2 mol % Pd(OAc)2 and 1.6 mol % tri-t-butylphosphine in 1.0 mL of toluene. After 6 hours, the reaction mixture was adsorbed onto silica gel and chromatographed with 2% ethyl acetate/hexanes to give 181 mg (83%) of N,N-dibutyl-o-toluidine. 1H NMR (500 MHz, CDCl3) δ 7.18 (t, J=7.8 Hz, 1H), 7.13 (d, J=7.8 Hz, 1H), 7.08 (d, J=7.8 Hz, 1H), 6.97 (t, J=7.8 Hz, 1H), 2.91 (t, J=7.5 Hz, 4H), 2.30 (s, 3H), 1.41-1.37 (m, 4H), 1.27 (sept, J=7.3 Hz, 4H), 0.87 (t, J=7.3 Hz, 6H). 13C NMR (125 MHz, CDCl3) δ 150.7, 135.0, 130.9, 126.0, 123.1, 122.3, 53.9, 29.6, 20.5, 18.3, 14.0.

Provenance & Evidence