10557-74-1

Usage

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 24, p. 43, 1987 DOI: 10.1002/jhet.5570240109

InChI:InChI=1/C9H6BrNO/c10-9-6-8(12-11-9)7-4-2-1-3-5-7/h1-6H

Upstream product

• 74213-24-4 N-dibromomethylidenehydroxylamine 
• 536-74-3 phenylacetylene 
• 13146-23-1 copper(I) phenylacetylenide 
• 107-18-6 allyl alcohol 
• 29636-75-7 3-bromo-1-phenylpropan-1-one 
• 6738-06-3 phenylethynylmagnesium bromide 
• 62847-52-3 3-nitro-1-phenyl-propan-1-one 

Downstream Products

• 942-68-7 3-methoxy-5-phenylisoxazole 
• 945-76-6 3-ethoxy-5-phenylisoxazole 
• 1006-67-3 5-phenylisoxazole 

Relevant academic research and scientific papers

Tandem synthesis of 3-halo-5-substituted isoxazoles from 1-copper(I) alkynes and dihaloformaldoximes

A tandem synthesis of 3-halo-5-substituted isoxazoles has been developed from 1-copper(I) alkynes and dihaloformaldoximes under base-free conditions. Thus, 1,3-dipolar cycloaddition and all its drawbacks can now be avoided completely.

Process for the preparation of 3,5-disubstituted isoxazoles

A novel process for the preparation of 3-bromo- and 3-chloro-5-substituted isoxazoles is provided. Dibromo- or dichloro-formaldoxime is reacted with an excess of an 1-alkyne derivative of the formula where R is hydrogen, phenyl or 1-6 C alkyl optionally substituted by halogen, OH, OR', CHO, COR', COOR', CONH2, CONR'R" or NHCOR' where, in turn, R' and R", which may be the same or different, are a 1-6 C alkyl or haloalkyl, in the presence of (i) at least an equimolecular amount, with respect to the dibromo- or dichloro-formaldoxime, of an alkaline base selected from the class consisting of sodium and potassium carbonate and bicarbonate and (ii) an inert solvent in which the 1-alkyne is soluble at room temperature.