2-(2-Bromophenyl)ethan-1-ol → Methyl 3-(4-((2-(2-hydroxyethyl)phenyl)ethynyl)phenyl)propanoate

Participants

Reaction Steps

The title compound was prepared from methyl 3-(4-ethynylphenyl)propanoate (107 mg, 0.57 mmol) and 2-bromophenethyl alcohol (100 μL, 0.74 mmol) according to the general procedure IF to give 83 mg (47%) of a dark orange oil after purification by flash chromatography (SiO2, EtOAc:PE, 1:1). Rf=0.19 (EtOAc:PE, 1:1); 1HNMR (CDCl3): δ 7.46-7.44 (m, 1H), 7.38-7.36 (m, 2H), 7.21-7.20 (m, 2H), 7.18-7.14 (m, 1H), 7.13-7.10 (m, 2H), 3.91-3.87 (m, 2H), 3.60 (s, 3H), 3.06 (t, J=5.1 Hz, 2H), 2.89 (t, J=5.7 Hz, 2H), 2.56 (t, J=5.4 Hz, 2H); 13CNMR (CDCl3): δ 173.1, 141.1, 140.4, 132.4, 131.7, 131.7, 129.7, 128.5, 126.6, 123.2, 121.2, 93.2, 87.6, 62.9, 51.7, 38.1, 35.4, 30.9.

Provenance & Evidence