3,5-Dimethylpyridine → 4-Chloro-3,5-dimethylpyridine

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Reaction Steps

Thionyl chloride was loaded into a reaction vessel equipped with a stirrer, a condenser, a dropping funnel, and a nitrogen bubbler. The temperature was lowered to 0-5ℑ C. and 3,5-lutidine was added dropwise, keeping the temperature between 0 and 10ℑ C. When the addition was complete the reaction mixture was refluxed for 18 hours. The mixture was cooled to 65ℑ C. and toluene (4 volumes) were added. 1.5 volumes of the mixture were distilled under vacuum. The heavy brown precipitate was collected by filtration. The crude product was recrystallized from methanol (3 volumes). Filtration afforded the product, 4-Chloro-3,5-Lutidine, as a beige solid, this was washed with methanol and dried under vacuum at 40ℑ C.; yield: 75%.

Provenance & Evidence