(1) Synthesis of 4-chloro-2,6-dimethylpyridine: 2,6-dimethyl-4-hydroxypyridine (1 g) was dissolved in phosphoryl chloride (5 mL). The reaction mixture was stirred at 100 °C for 6 hours. Upon completion of the reaction, the reaction was quenched by the slow addition of water, followed by adjusting the pH to neutral with 5N aqueous sodium hydroxide and liquid-liquid extraction with ethyl acetate. The organic layers were combined, washed with saturated brine and then dried with anhydrous magnesium sulfate. The desiccant was removed by filtration and the filtrate was concentrated under reduced pressure to afford the target product 4-chloro-2,6-dimethylpyridine (1.15 g). The product was characterized by 1H-NMR (400 MHz, CDCl3): δ (ppm) 2.51 (s, 6H), 6.99 (s, 2H).
