1,2-Dimethoxyethane → 4-(4-Methoxyphenyl)pyridine

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-methoxybenzene boronic acid (2 g, 13.15 mmol), 4-bromopyridine hydrochloride (3.84 g, 19.72 mmol), diphenylphosphinobutylpalladium (II) dichloride (100 mg), dimethoxyethane (50 ml) and 2M sodium carbonate solution (30 ml) were stirred at 85° C. for 1.5 hours under a nitrogen atmosphere. The solution was allowed to cool to ambient temperature, diluted with ethyl acetate (150 ml) and washed with water (150 ml). The aqueous layer was extracted with ethyl acetate (2×100 ml). The combined organic layers were dried over sodium sulphate and the solvents were removed leaving a white solid, which was chromatographed on silica gel in 70-100% ethyl acetate/hexane giving the title compound as a white solid (1.95 g, 80%). 1H NMR (250 MHz, CDCl3) δ 8.66-8.63 (2H, d, J=6.2 Hz), 7.63-7.59 (2H, d, J=9.0 Hz), 7.50-7.47 (2H, d, J=6.2 Hz), 7.03-6.99 (2H, d, J=9.0 Hz), and 3.87 (3H, s). m/z (ES+) 186 (M+1).

Provenance & Evidence