1-Bromo-2-ethylbenzene → Methyl 3-(4-((2-ethylphenyl)ethynyl)phenyl)propanoate

Participants

Reaction Steps

The title compound was prepared from methyl 3-(4-ethynylphenyl)propanoate (95 mg, 0.51 mmol) and 1-bromo-2-ethylbenzene (0.10 mL, 0.73 mmol) according to the general procedure IF to give 130 mg (87%) of a clear oil after purification by flash chromatography (SiO2, EtOAc:PE, 1:7): Rf=0.28 (EtOAc:PE, 1:4); 1H NMR (CDCl3) δ 7.50-7.48 (m, 1H), 7.46-7.44 (m, 2H), 7.26-7.22 (m, 2H), 7.20-7.14 (m, 3H), 3.67 (s, 3H), 2.96 (t, J=7.8 Hz, 2H), 2.88 (q, J=7.2 Hz, 2H), 2.63 (t, J=7.6 Hz, 2H), 1.29 (t, J=7.6 Hz, 3H); 13C NMR (CDCl3) δ 173.2, 146.3, 140.9, 132.2, 131.8, 128.6, 128.5, 128.1, 125.8, 122.5, 121.7, 92.9, 88.0, 51.8, 35.6, 31.0, 27.9, 14.9; ESI-MS m/z 315.1 (M+Na+).

Provenance & Evidence