3-Iodotoluene → HCID 58319104, compound

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Reaction Steps

The title compound was prepared from methyl 3-(4-ethynylphenyl)propanoate (90 mg, 0.48 mmol) and iodo-3-methylbenzene (0.07 mL, 0.55 mmol) according to the general procedure IB to give 42 mg (36%) of an orange oil after purification by flash chromatography (SiO2, EtOAc/hexanes, 1:30→1:10). Rf: 0.29 (EtOAc:hexanes, 1:5); 1HNMR (CDCl3) δ 7.46-7.43 (m, 2H), 7.35-7.31 (m, 2H), 7.22-7.12 (m, 4H), 3.67 (s, 3H), 2.99-2.93 (t, 2H, J=7.8 Hz), 2.66-2.61 (t, 2H, J=7.8 Hz), 2.35 (s, 3H); 13CNMR (CDCl3) δ 173.1, 140.8, 138.0, 132.1, 131.7, 129.1, 128.6, 128.3, 128.2, 123.1, 121.3, 89.3, 88.9, 51.6, 35.4, 30.8, 21.2; ESI-MS m/z 301.1 (MNa+).

Provenance & Evidence