Toluene → HCID 20802836, compound

Participants

Reaction Steps

A mixture of 5-Bromo-3-acetylpyridine (2 g, 10 mmol), phenylboronic acid (1.5 g, 12 mmol), trans-dibromobis(triphenylphosphine) palladium (II) (0.4 g, 0.5 mmol), toluene (60 ml), ethanol (20 ml) and 2M aqueous sodium carbonate (40 ml) was refluxed for 1 hour under a nitrogen atmosphere. The mixture was diluted with ethyl acetate and the organic phase was washed with water and brine, dried and evaporated. The crude product was chromatographed on silica gel eluting with a gradient of 0-100% EtoAc in hexane to afford the: 5-(Phenyl)-3-acetylpyridine as a solid. 2 g (10 mmol, 100%). TLC Rf 0.3 (1:1 hexane/EtOAc); MS: 198.5 (M+H); 1H NMR (DMSO) δ 9.12 (dd, J=2.2 Hz, 2H), 8.50 (t, J=2.1 Hz, 1H), 7.83 (d, J=8.1 Hz, 2H), 7.54 (t, J=7.7 Hz, 2H), 7.49 (t, J=7.7 Hz, 1H), 3.02 (s, 3H); 13C NMR δ 197.51, 151.30, 148.12, 136.14, 135.51, 134.05, 133.34, 132.00, 129.91, 129.78, 129.19, 127.64, 27.14.

Provenance & Evidence