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A mixture of 4-bromopyridine hydrochloride (7.5 g, 38.6 mmol) and 2-fluorobenzeneboronic acid (6.75 g, 48 mmol) in tetrahydrofuran (80 ml) and 2M sodium carbonate (58 ml) was degassed with nitrogen for 20 min then tetrakis(triphenylphosphine)palladium(0) (1.34 g, 1.2 mmol) was added and the reaction heated at reflux for 24 h. The mixture was cooled to ambient temperature then partitioned between ethyl acetate and 10% sodium carbonate. The organics were washed with water, saturated sodium hydrogencarbonate, dried over anhydrous magnesium sulfate, filtered and pre-adsorbed onto silica. Purification by chromatography on silica eluting with isohexane (containing 0.5% triethylamine) on a gradient of ethyl acetate (20-40%) afforded 4-(2-fluorophenyl)pyridine as a yellow oil that crystallised on standing (6.26 g, 94%): δH (400 MHz, CDCl3) 7.17-7.22 (1H, m), 7.26 (1H, ddd, J 8, 8 and 1), 7.38-7.44 (1H, m), 7.47-7.50 (3H, m), 8.68 (2H, d, J 4); m/z (ES+) 174 (M++H).

1. customwas degassed with nitrogen for 20 min
2. temperaturethe reaction heated
3. temperatureat reflux for 24 h
4. customthen partitioned between ethyl acetate and 10% sodium carbonate
5. washThe organics were washed with water, saturated sodium hydrogencarbonate
6. dry with materialdried over anhydrous magnesium sulfate
7. filtrationfiltered and pre-adsorbed onto silica
8. customPurification by chromatography on silica eluting with isohexane (containing 0.5% triethylamine) on a gradient of ethyl acetate (20-40%)