4-Iodotoluene → Ethyl 2-(4-(p-tolylethynyl)phenoxy)acetate

Participants

Reaction Steps

The title compound was prepared from ethyl (4-ethynylphenoxy)acetate (41 mg, 0.20 mmol) and iodo-4-methylbenzene (46 mg, 0.21 mmol) according to the general procedure ID to give 47 mg (79%) of an orange oil after purification by flash chromatography (SiO2, EtOAc/hexanes, 1:10). Rf: 0.14 (EtOAc:hexanes, 1:10); 1HNMR (CDCl3) δ 7.49-7.37 (m, 4H), 7.17-7.11 (m, 2H), 6.91-6.84 (m, 2H), 4.63 (s, 2H), 4.29-4.26 (dq, 2H, J=7.2 Hz, 2.1 Hz), 2.36 (s, 3H), 1.32-1.27 (tt, 3H, J=7.2 Hz, 1.5 Hz); 13CNMR (CDCl3) δ 168.6, 157.6, 138.1, 133.0, 131.4, 129.1, 120.3, 116.8, 114.7, 88.6, 88.3, 65.4, 61.5, 21.5, 14.1; EI-MS m/z 294 (M+).

Provenance & Evidence