3-Iodotoluene → Ethyl 2-(4-(o-tolylethynyl)phenoxy)acetate

Participants

Reaction Steps

The title compound was prepared from ethyl (4-ethynylphenoxy)acetate (42 mg, 0.21 mmol) and iodo-3-methylbenzene (0.03 mL, 0.20 mmol) according to the general procedure ID to give 43 mg (72%) of an orange oil after purification by flash chromatography (SiO2, EtOAc/hexanes, 1:10). Rf: 0.22 (EtOAc:hexanes, 1:10); 1HNMR (CDCl3) δ 7.49-7.46 (m, 3H), 7.26-7.12 (m, 3H), 6.90-6.87 (m, 2H), 4.64 (s, 2H), 4.30-4.27 (dq, 2H, J=7.2 Hz, 2.1 Hz), 2.50 (s, 3H), 1.33-1.28 (tt, 3H, J=7.2 Hz, 1.5 Hz); 13CNMR (CDCl3) δ 168.6, 157.7, 140.0, 133.0, 131.7, 129.4, 128.1, 125.5, 123.2, 116.9, 114.7, 93.0, 87.4, 65.4, 61.5, 20.7, 14.1; EI-MS m/z 294 (M+).

Provenance & Evidence