2-Iodotoluene → Methyl 3-(4-(o-tolylethynyl)phenyl)propanoate

Participants

Reaction Steps

The title compound was prepared from methyl 3-(4-ethynylphenyl)propanoate (90 mg, 0.48 mmol) and iodo-2-methylbenzene (0.07 mL, 0.55 mmol) according to the general procedure IB to give 36 mg (31%) of an orange oil after purification by flash chromatography (SiO2, EtOAc/hexanes, 1:30→1:10). Rf: 0.27 (EtOAc:hexanes, 1:5); 1HNMR (CDCl3) δ 7.49-7.44 (m, 3H), 7.23-7.17 (m, 5H), 3.67 (s, 3H), 2.99-2.94 (t, 2H, J=7.8 Hz), 2.66-2.61 (t, 2H, J=7.8 Hz), 2.50 (s, 3H); 13CNMR (CDCl3) δ 173.1, 140.8, 140.1, 131.8, 131.6, 129.4, 128.3, 128.2, 125.5, 123.1, 121.5, 93.2, 88.1, 51.6, 35.4, 30.8, 20.7; ESI-MS m/z 301.1 (MNa+).

Provenance & Evidence