Peracetic Acid → 5-Chloro-6-isobutoxypyridin-3-OL

Participants

Reaction Conditions

Reaction Steps

To a suspension of 5-chloro-6-isobutoxypyridin-3-ylboronic acid (3.02 g, 13.1 mmol) in acetic acid/water (1:1 20 mL) cooled to 0° C. was slowly added peracetic acid (3.9 mL, 20.0 mmol) and the reaction mixture was maintained at 0° C. for 1.5 hours and then at room temperature for 1 hour. Additional peracetic acid (3.9 mL, 20.0 mmol) was added and the reaction stirred at room temperature for 40 minutes after which time the suspension dissolved. The reaction mixture was quenched with sodium thiosulphate solution (15 mL) and stirred for 5 minutes. The mixture was extracted with ethyl acetate (2×30 mL) and the combined organic extracts washed with brine (30 mL), dried over magnesium sulphate and filtered. The solvent was removed under reduced pressure to give a yellow oil (3.66 g). Purification by flash column chromatography (Biotage™ 50 g silica cartridge) eluting with a gradient of dichloromethane/methanol (100% to 90% to 80%) gave the title compound (1.94 g, 73%) as a white solid.

Provenance & Evidence