3-Iodotoluene → Ethyl 2-(4-(m-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 (0.04 mL, 0.31 mmol) according to the general procedure ID to give 56 mg (93%) of an orange oil after purification by flash chromatography (SiO2, EtOAc/hexanes, 1:10). Rf: 0.44 (EtOAc:hexanes, 1:5); 1HNMR (CDCl3) δ 7.61-7.56 (m, 2H), 7.51-7.31 (m, 4H), 7.03-6.88 (m, 2H), 4.75 (s, 2H), 4.43-4.36 (dq, 2H, J=7.2 Hz, 2.1 Hz), 2.47 (s, 3H), 1.44-1.38 (tt, 3H, J=7.2 Hz, 1.5 Hz); 13CNMR (CDCl3) δ 168.6, 157.7, 138.0, 133.1, 132.0, 128.9, 128.5, 128.2, 123.2, 116.2, 114.7, 88.6, 88.6, 65.4, 61.5, 21.2, 14.1; EI-MS m/z 294 (M+).

Provenance & Evidence