Benzenamine, 3-ethynyl- → Methyl 3-(4-((3-aminophenyl)ethynyl)phenyl)propanoate

Participants

Reaction Steps

The title compound was prepared from methyl 3-(4-iodophenyl)propanoate (100 mg, 0.34 mmol) and 3-ethynylaniline (0.04 mL, 0.38 mmol) according to the general procedure IC to give 89 mg (93%) of an orange solid after purification by flash chromatography (SiO2, EtOAc/hexanes, 1:3). Rf: 0.35 (EtOAc:hexanes, 1:1); 1HNMR (CDCl3) δ 7.44-7.42 (m, 2H), 7.18-7.09 (m, 3H), 6.93-6.91 (m, 1H), 6.83 (s, 1H), 6.66-6.63 (m, 1H), 3.66 (s, 3H), 2.98-2.93 (t, 2H, J=7.8 Hz), 2.65-2.60 (t, 2H, J=7.8 Hz); 13CNMR (CDCl3) δ 173.1, 146.3, 140.7, 131.7, 129.2, 128.3, 124.0, 122.0, 121.3, 117.7, 115.2, 89.3, 88.6, 51.6, 35.4, 30.8; EI-MS m/z 279 (M+).

Provenance & Evidence