Synthesis of 3-Haloisoxazolines by Deoxygenation of 3-Haloisoxazoline N-Oxides under Treatment with Acetyl Bromide

摘要

A method for the preparation of 4,5-disubstituted 3-halo- (chloro-, bromo-) isoxazolines was developed. Acetyl bromide was found to be a convenient reducing agent for 3-halosubstituted isoxazoline N-oxides affording target deoxygenated derivatives in good yields. Compared to the literature examples, presented approach for the synthesis of 3-haloisoxazolines is regioselective and does not require the use of hazardous phosgene oximes. Selective transformations of the obtained products were demonstrated.