4-Iodotoluene → Methyl 3-(4-(p-tolylethynyl)phenyl)propanoate

Participants

Reaction Steps

The title compound was prepared from methyl 3-(4-ethynylphenyl)propanoate (90 mg, 0.48 mmol) and iodo-4-methylbenzene (0.07 mL, 0.55 mmol) according to the general procedure IB to give 18 mg (15%) of an orange oil after purification by flash chromatography (SiO2, EtOAc/hexanes, 1:30→1:10). Rf: 0.42 (EtOAc:hexanes, 1:5); 1HNMR (CDCl3) δ 7.45-7.39 (m, 4H), 7.18-7.13 (m, 4H), 3.67 (s, 3H), 2.98-2.93 (t, 2H, J=7.8 Hz), 2.66-2.60 (t, 2H, J=7.8 Hz), 2.36 (s, 3H); 13CNMR (CDCl3) δ 173.1, 140.6, 138.3, 131.7, 131.4, 129.1, 128.3, 121.4, 120.2, 89.3, 88.6, 51.6, 35.4, 30.8, 21.5; EI-MS m/z 278 (M+).

Provenance & Evidence