Iodine → Methyl 2,4-dichloro-3-(3-methylisoxazol-5-yl)benzoate

Participants

Reaction Steps

4.7 g (55.6 mmol) of sodium bicarbonate in 50 ml of water were added to 4.0 g (13.9 mmol) of methyl 2,4-dichloro-(2-hydroxyiminobut-3-en-4-yl)benzoate in 100 ml of tetrahydrofuran. Under the exclusion of light, 7.9 g (47.8 mmol) of potassium iodide and 3.7 g (14.6 mmol) of iodine in 50 ml of water were then added and the mixture was heated under reflux for 4 hours. The mixture was then cooled and 100 ml of a 24% strength sodium pyrosulfite solution were added a little at a time and the solution was extracted with diethyl ether and concentrated. The residue was subsequently chromatographed over silica gel (eluent: cyclohexane:ethyl acetate=9:1). 2.4 g (60% of theory) of methyl 2,4-dichloro-3-(3-methylisoxazol-5-yl)benzoate were obtained.

Provenance & Evidence