The Korean Journal of Pesticide Science (농약과학회지)

The Korean Society of Pesticide Science (한국농약과학회)
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New method for the synthesis of 3-chloro-2-(4-chloro-2-fluoro-5-hydroxyphenyl)-4,5,6,7-tetrahydro-2H-indazole

3-Chloro-2-(4-chloro-2-fluoro-5-hydroxyphenyl)-4,5,6,7-tetrahydro-2H-indazole의 제조방법에 관한 연구

  • Published : 2005.03.31
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Abstract

3-Chloro-2-(4-chloro-2-fluoro-5-hydroxyphenyl)-4,5,6,7-tetrahydro-2H-indazole, which is the key intermediate of cyclic imide type compounds such as EK 5439 and S-275 series, were practically synthesized by the procedure of hydrolysis of by-products and were produced in the reaction of 2-(2-fluoro-4-chloro-5-hydroxyphenyl)-2,3a,4,5,6,7-hexahydroindazol-3-one with phosgene.

Protox 저해제인 cyclic imide type 화합물 중에서 EK 5439와 S-275 같은 화합물들의 필수 중간체인 3-chloro-2-(4-chloro-2-fluoro-5-hydroxyphenyl)-4,5,6,7-tetrahydro-2H-indazole은 2-(2-fluoro-4-chloro-5-hydroxyphenyl)-2,3a,4,5,6,7-hexahyoindazol-3-one을 포스겐과 반응시켜서 얻을 수 있다고 알려져 있으나, 수율이 매우 낮고 재현성이 없다. 따라서 이 반응의 부산물들을 분리 확인하여, 이 부산물들이 반응물과 목적물의 이량체임을 밝히고, 이들을 가수분해함으로서 목적물의 합성수율을 높이고 반응물을 거의 대부분 회수할 수 있는 효과적인 방법을 개발하였다.

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References

  1. Hirai, K. (1999) Structural evolution and synthesis of diphenyl ethers, cyclic imides and related compounds. pp.15-71, In Peroxidising herbicides (ed. Boger, P. and K. Wakabayashi), Springer, Berlin
  2. Nagano, E., I. Takemoto, M. Fukushima, R. Yoshida, and H. Matsumoto (1983) Herbicidal 2-substitutedphenyl-4,5,6,7-tetrahydro-2H-indazoles. GB 2127410A
  3. Ryu, E. K., D. J. Jeon, J. H. Song, H. R. Kim, J. N. Lee, K. M. Kim, and K. Y. Cho (2001) Herbicidal 2-(5-isoxazolinylmethoxyphenyl)-4,5,6,7-tetrahydro-2H-in dazo1e derivatives. Korean Patent. 0289470
  4. Ryu, E. K., D. J. Jeon, J. H. Song, H. R. Kim, and K. Y. Park (2002) Improved synthetic method of 3-chloro-2-(4-chloro-2-fluoro-5-hydroxyphenyl)-4,5,6,7-te trahydro-2H-indazole. Korean Patent. 0033207