Ring Opening of 3‐Bromo‐2‐Isoxazolines to β‐Hydroxy Nitriles

Abstract

3‐Bromo‐2‐isoxazolines were converted to the corresponding β‐hydroxy nitriles by treatment with sodium iodide in the presence of either chlorotrimethylsilane or para‐toluenesulfonic acid. Both methods gave β‐hydroxy nitriles under relatively mild conditions in good to moderate yields for a variety of substituted 3‐bromo‐2‐isoxazolines.

Keywords:

• Bromoformaldoxime
• Bromoisoxazolines
• β‐Hydroxynitriles
• Iodotrimethylsilane
• para‐Toluenesulfonic acid