To a mixture of 1-bromo-4-(3-chloropropoxy)benzene (1.25 g) and tetrakistriphenylphosphinepalladium (58 mg) in toluene (12 mL) and potassium carbonate (2.07 g) in water (6 mL) is added pyridine-4-boronic acid (380 mg) dissolved in ethanol. The mixture is heated for five hours at a temperature close to 80° C. Solvents are removed under reduced pressure and the residue dissolved in ethyl acetate. The organic phase is washed with a 10% aqueous solution of potassium hydroxide, then with water, dried over magnesium sulfate, filtered and concentrated. The residue is purified by chromatography over silica gel (eluent dichloromethane/methanol from 100/0 to 95/5) to give 408 mg of 4-(4-(3-chloropropoxy)phenyl]pyridine as an ochre oil used without further purification.
