Synthesis of (4-bromo-3-(4-chlorophenyl)isoxazol-5-yl)methanol as a New Compound

Heterocycles are an important class of compounds, not only because of their natural abundance, but also of their chemical, biological and technical significances. Above all the heterocycles, isoxazole is one of the most useful compounds, which was found as an important unit in many biologically active compounds [1]. In this research work, some new compounds of isoxazole family were synthesized and characterized. First, 4-chlorobenzaldehyde (1) was transformed to 4-chlorobenzaldoxime (2) by using NH2OH in pyridine. The in situ generated nitriloxide from reaction between (2) and NaOCl, was reacted with propargylalcohol to produce 3-(4-chlorophenyl)-5-hydroxymethyl isoxazole (3) in a cycloaddition procedure. The required bromo-derivative of the synthesized isoxazole (4) was obtained from reaction of (3) and Br2 and produced (4-bromo-3-(4-chlorophenyl)isoxazol-5-yl)methanol (4). The structure of all the synthesized compounds was characterized and confirmed by FT-IR and NMR spectroscopy techniques.