2-Iodophenylacetonitrile → Methyl 3-(4-((2-(cyanomethyl)phenyl)ethynyl)phenyl)propanoate

Participants

Reaction Steps

The title compound was prepared from methyl 3-(4-ethynylphenyl)propanoate (74 mg, 0.39 mmol) and 2-(2-iodophenyl)acetonitrile (60 μL, 0.43 mmol) according to the general procedure IC to give 74 mg (62%) of an orange solid after purification by flash chromatography (SiO2, EtOAc:PE, 1:4). Rf=0.08 (EtOAc:PE, 1:4); 1H NMR (CDCl3) δ 7.55-7.46 (m, 4H), 7.37-7.34 (m, 2H), 7.21 (d, J=8.4 Hz, 2H), 3.96 (s, 2H), 3.67 (s, 3H), 2.97 (t, J=7.7 Hz, 2H), 2.64 (t, J=7.5 Hz, 2H); 13C NMR (CDCl3) δ 173.0, 141.6, 132.3, 131.7, 131.6, 128.9, 128.5, 128.1, 122.9, 120.4, 117.4, 95.6, 85.7, 51.7, 35.3, 30.8, 22.7; ESI-MS m/z 326.1 (M+Na+).

Provenance & Evidence