3-Iodobenzonitrile → HCID 67072629, compound

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Reaction Steps

The title compound was prepared from methyl 3-(4-ethynylphenyl)propanoate (103 mg, 0.55 mmol) and 3-iodobenzonitrile (134 mg, 0.59 mmol) according to the general procedure IC to give 68 mg (58%) of an orange-brown solid after purification by flash chromatography (SiO2, EtOAc/hexanes, 1:5). Rf: 0.26 (EtOAc:hexanes, 1:5); 1HNMR (CDCl3) δ 7.79-7.78 (m, 1H), 7.73-7.70 (m, 1H), 7.61-7.57 (m, 1H), 7.48-7.43 (m, 3H), 7.22-7.18 (m, 2H), 3.67 (s, 3H), 3.00-2.95 (t, 2H, J=7.8 Hz), 2.67-2.62 (t, 2H, J=7.8 Hz); 13CNMR (CDCl3) δ 173.0, 141.7, 135.5, 134.8, 131.9, 131.3, 129.2, 128.5, 125.0, 120.2, 118.1, 116.7, 112.8, 91.7, 86.6, 51.7, 35.3, 30.8; EI-MS m/z 289 (M+).

Provenance & Evidence