3-Bromo-o-xylene → Methyl 3-(4-((2,3-dimethylphenyl)ethynyl)phenyl)propanoate

Participants

Reaction Steps

The title compound was prepared from methyl 3-(4-ethynylphenyl)propanoate (99 mg, 0.53 mmol) and 1-bromo-2,3-dimethylbenzene (0.08 mL, 0.59 mmol) according to the general procedure IC to give 22 mg (14%) of an orange oil after purification by flash chromatography (SiO2, EtOAc/hexanes, 1:5). Rf: 0.42 (EtOAc:hexanes, 2:5); 1HNMR (CDCl3) δ 7.47-7.44 (m, 2H), 7.37-7.34 (m, 1H), 7.19-7.17 (m, 2H), 7.12-7.03 (m, 2H), 3.67 (s, 3H), 2.99-2.94 (t, 2H, J=7.8 Hz), 2.66-2.61 (t, 2H, J=7.8 Hz), 2.45 (s, 3H), 2.29 (s, 3H); 13CNMR (CDCl3) δ 173.7, 142.7, 137.8, 132.2, 130.8, 130.5, 129.6, 126.4, 124.0, 122.1, 93.5, 89.2, 35.6, 31.4, 20.3, 17.6; ESI-MS m/z 315.1 (MNa+).

Provenance & Evidence