1,2-Dimethoxyethane → 4-(4-(Trifluoromethoxy)phenyl)pyridine

Beteiligte Stoffe

Reaktionsschritte

A mixture of 4-(trifluoromethoxy)benzene boronic acid (2 g, 9.7 mmol), 4-bromopyridine hydrochloride (2.83 g, 14.5 mmol), diphenylphosphinobutylpalladium (II) dichloride (100 mg), dimethoxyethane (50 ml) and a 2M sodium carbonate solution (30 ml) were stirred at 85° C. for 2 hours. The solution was allowed to cool to ambient temperature diluted with water (100 ml), and extracted with ethyl acetate (2×100 ml). The combined organic layers were dried over sodium sulphate. Removal of the solvents in vacuo gave an oil which was chromatographed on silica in 30% ethyl acetate/hexane giving the title compound as an oil (1.86 g, 80%). 1H NMR (250 MHz, CDCl3) δ 8.72-8.70 (2H, d, J=6.2 Hz), 7.69-7.63 (2H, d, J=9.6 Hz), 7.49-7.47 (2H, d, J=6.2 Hz), and 7.36-7.32 (2H, d, J=9.6 Hz). m/z (ES+) 240 (M+1).

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