Example 7 Synthesis of 2-(chloromethyl)-4,6-dimethylpyridine: 121.18 g (1 mol) of 2,4,6-trimethylpyridine was dissolved in 400 mL of chloroform and heated to reflux. 140 g (0.6 mol) of trichloroisocyanuric acid (≥90% effective chlorine content) was added slowly over 4 h. Stirring was continued for 30 min after addition. The reaction mixture was cooled and filtered and the filtrate was mixed with 150 mL of 10% hydrochloric acid to transfer the product to the aqueous phase. The aqueous phase was separated, washed with 150 mL of ethyl acetate and adjusted to alkaline with sodium hydroxide solution. The aqueous phase was then extracted with 100 mL of ethyl acetate, and the organic phases were combined, dried and concentrated under reduced pressure to give 45 g (28.9% yield) of 2-(chloromethyl)-4,6-dimethylpyridine. The product had a chlorine content of 22.78% (theoretical value 22.78%) and a boiling point of 64-70°C (1 mmHg).
