Trichloroisocyanuric Acid → 3-Chloro-6-(chloromethyl)pyridazine

Participants

Reaction Steps

To a refluxing solution of 3-chloro-6-methylpyridazine (5.0 g, 39 mmol) in chloroform (75 mL) was added trichloroisocyanuric acid (3.6 g, 16 mmol) portionwise. The solution was allowed to reflux overnight, after which the crude reaction mixture was filtered, washed with 1 M sodium hydroxide (NaOH), and the organic phase was dried over magnesium sulfate. The crude product was concentrated under reduced pressure and purified by silica gel chromatography to furnish 3-chloro-6-chloromethyl-pyridazine (D) as a yellow oil which upon sitting became a brown solid=2.9 g (46%).

Provenance & Evidence