Synthesis

Convenient and improved halogenation of 3, 5-diarylisoxazoles using N-halosuccinimides

RA Day, JA Blake, CE Stephens

Index: Day, Ruth Ann; Blake, Jacqueline A.; Stephens, Chad E. Synthesis, 2003 , # 10 p. 1586 - 1590

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Citation Number: 25

Abstract

Abstract The convenient C-4 halogenation of 3, 5-diarylisoxazoles using N- halosuccinimides (NBS, NCS, or NIS) in acetic acid is described. A strong acid catalyst was required for efficient halogenation of some isoxazoles depending on the substituent on the 5- phenyl ring. Finally, the 4-iodoisoxazoles were found to undergo a novel proto-deiodination upon heating in the presence of H 2 SO 4.

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