Iodine → 2-Chloro-3-hydroxy-4-iodo-6-(1-hydroxyethyl)-pyridine

Participants

Reaction Steps

2-Chloro-3-hydroxy-6-(1-hydroxyethyl)-pyridine (4.5 g, 23.6 mmole) is suspended in 70 ml water in a 200 ml one neck round bottom flask. The suspension is treated successively with potassium carbonate (6.5 g, 47.2 mmole) and iodine (12.0 g, 47.2 mmole) and the reaction mixture is stirred 4 h at room temperature. The excess iodine is quenched with saturated sodium thiosulfate and the pH of the reaction mixture is adjusted to 3 with 10% hydrochloric acid. The solid is collected, washed with water, and is taken up in ethyl acetate. The organic layer is dried over magnesium sulfate and is concentrated in vacuo to a yellow solid. The solid is washed with chloroform and is dried to provide 4.4 g (62%) of 2-chloro-3-hydroxy-4-iodo-6-(1-hydroxyethyl)-pyridine.

Provenance & Evidence