2-Bromotoluene → 4-o-tolylmorpholine

Participants

Reaction Steps

The above general procedure was followed using 2-bromotoluene (171 mg, 1.10 mmol) and morpholine (87 mg, 1.00 mmol) with 1 mol % Pd(OAc)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 using 5% ethyl acetate/hexanes to give 179 mg (>99%) of N-(2-methylphenyl)morpholine. 1H NMR (500 MHz, CDCl3) δ 7.20 (d J=7.4 Hz, 1H), 7.18 (d, J=7.4 Hz, 1H), 7.03 (d, J=7.4 Hz, 1H), 7.01 (d, J=7.4 Hz, 1H), 3.86 (t, J=4.5 Hz, 4H), 2.92 (t, J=4.5 Hz, 4H), 2.33 (s, 3H). 13C NMR (125 MHz, CDCl3) δ 151.4, 132.7, 131.2, 126.7, 123.5, 119.0, 67.5, 52.4, 17.8.

Provenance & Evidence