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Efficient and Practical Route for 3,5-Dichloro-4-(1,1,2,2-tetrafluoroethoxy)aniline: a Key Intermediate of Hexaflumuron

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Abstract

An improved and practical route is reported here for accessing 3,5-dichloro-4-(1,1,2,2-tetrafluoroethoxy)aniline (1), a key intermediate of hexaflumuron. The overall yield for the preparation of 1 is 74.0%, with a purity of 99.7%, after a one-pot process with catalytic hydrogenation and Bamberger rearrangement and a greener addition reaction in a continuous flow reactor. Compared with the original process route, the new synthetic route has the advantages of fewer reaction steps, higher overall yield, less process safety hazard and environmental impact.

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REFERENCES

  1. Wellinga, K., Mulder, R., and Dallen, J.V., J. Agric. Food Chem., 1973, vol. 21, p. 348. https://doi.org/10.1021/jf60187a052

    Article  CAS  PubMed  Google Scholar 

  2. Qian, X.H., J. Agric. Food Chem., 1999, vol. 47, p. 4415. https://doi.org/10.1021/jf981174r

    Article  CAS  PubMed  Google Scholar 

  3. Nakagawa, Y., Kitahara, K., Nishioka, T., Iwamura, H., and Fujita, T., Pestic. Biochem. Physiol., 1984, vol. 21, p. 309. https://doi.org/10.1016/0048-3575(84)90099-3

    Article  CAS  Google Scholar 

  4. Tecle, B., Ruzo, L.O., and Casida, J.E., J. Agric. Food Chem., 1988, vol. 36, p. 178. https://doi.org/10.1021/jf00079a045

    Article  CAS  Google Scholar 

  5. Yoon, C., Yang, J.O., Kang, S.H., and Kim, G.H., J. Pestic. Sci., 2008, vol. 33, p. 44. https://doi.org/10.1584/jpestics.G07-09

    Article  CAS  Google Scholar 

  6. Grosscurt, A.C., Van, H.R., and Wellinga, K., J. Agric. Food Chem., 1979, vol. 27, p. 406. https://doi.org/10.1021/jf60222a061

    Article  CAS  Google Scholar 

  7. Chen, L., Wang, Q.M., Huang, R.Q., Mao, C.H., Shang, J., and Bi, F.C., J. Agric. Food Chem., 2005, vol. 53, p. 38. https://doi.org/10.1021/jf048561n

    Article  CAS  PubMed  Google Scholar 

  8. Chen, L. Huang, Z.Q., Wang, Q.M., Shang, J., Huang, R.Q., and Bi, F.C., J. Agric. Food Chem., 2007, vol. 55, p. 2659. https://doi.org/10.1021/jf063564g

    Article  CAS  PubMed  Google Scholar 

  9. Sun, R.F., Zheng, Y.L., Chen, L., Li, Y.Q., Li, Q.S., Song, H.B., Huang, R.Q., Bi, F.C., and Wang, Q.M., J. Agric. Food Chem., 2009, vol. 57, p. 3661. https://doi.org/10.1021/jf900324a

    Article  CAS  PubMed  Google Scholar 

  10. Huang, Q.C., Wu, X.W., Yu, X.Q., Zhang, L., Lu, M.Q., and Tao, L.M., Environ. Toxicol. Chem., 2015, vol. 34, p. 1675. https://doi.org/10.1002/etc.2969

    Article  CAS  PubMed  Google Scholar 

  11. Ruan, W.L., Yi, J.H., Lu, H.F., and Guo, S., Agrochem., 2012, vol. 51, p. 184. https://doi.org/10.16820/j.cnki.1006-0413.2012.03.011

    Article  CAS  Google Scholar 

  12. Wang, G.L., Wang, F., Nie, Q.C., Wang, G., Xu, L., and Ding, K.H., Agrochem., 2021, vol. 60, p. 11. https://doi.org/10.16820/j.cnki.1006-0413.2021.01.003

    Article  CAS  Google Scholar 

  13. Wu, W.L., Yang, J.Y., Zou, X.Y., Yin, K., Yan, Z.H., and He, X.S., World Pestic., 2022, vol. 44, p. 45. https://doi.org/10.16201/j.cnki.cn10-1660/tq.2022.04.06

    Article  Google Scholar 

  14. Movsisyan, M., Delbeke, E.I.P., Berton, J.K.E.T., Battilocchio, C., Ley, S.V., and Stevens, C.V., Chem. Soc. Rev., 2016, vol. 45, p. 4892. https://doi.org/10.1039/C5CS00902B

    Article  CAS  PubMed  Google Scholar 

  15. Porta, R., Benaglia, M., and Puglisi, A., Org. Process Res. Dev., 2016, vol. 20, p. 2. https://doi.org/10.1021/acs.oprd.5b00325

    Article  CAS  Google Scholar 

  16. Britton, J. and Raston, C.L., Chem. Soc. Rev., 2017, vol. 46, p. 1250. https://doi.org/10.1039/C6CS00830E

    Article  CAS  PubMed  Google Scholar 

  17. Bogdan, A.R. and Dombrowski, A.W., J. Med. Chem., 2019, vol. 62, p. 6422. https://doi.org/10.1021/acs.jmedchem.8b01760

    Article  CAS  PubMed  Google Scholar 

  18. Baumann, M., Moody, T.S., Smyth, M., and Wharry, S., Org. Process Res. Dev., 2020, vol. 24, p. 1802. https://doi.org/10.1021/acs.oprd.9b00524

    Article  CAS  Google Scholar 

  19. Sun, M.L., Yang, J.X., Fu, Y.T., Liang, C.M., Li, H., Yan, G.M., Yin, C., Yu, W., Ma, Y.Y., Chen, R.H., and Ye, J.X., Org. Process Res. Dev., 2021, vol. 25, p. 1160. https://doi.org/10.1021/acs.oprd.0c00543

    Article  CAS  Google Scholar 

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Funding

This work was supported by the National Natural Science Foundation of China (no. 21878047), the Fundamental Research Funds for the Central Universities (2242020K1G001), and a Project Funded by the Priority Academic Program Development of Jiangsu Education Institutions (PAPD) (1107047002).

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Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, Southeast University, 211189, Nanjing, China

    Kai Yin, Lei Fang & Yiwei Zhang

  2. Zhejiang Nanjiao Chemistry Co., Ltd., 312369, Shaoxing, China

    Kai Yin & Hao Wu

  3. Stone Laboratory Co., Ltd., 266045, Qingdao, China

    Qi Yin

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  1. Kai Yin
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  2. Hao Wu
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  3. Qi Yin
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  4. Lei Fang
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  5. Yiwei Zhang
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Correspondence to Kai Yin or Yiwei Zhang.

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Yin, K., Wu, H., Yin, Q. et al. Efficient and Practical Route for 3,5-Dichloro-4-(1,1,2,2-tetrafluoroethoxy)aniline: a Key Intermediate of Hexaflumuron. Russ J Org Chem 59 (Suppl 1), S1–S6 (2023). https://doi.org/10.1134/S1070428023130018

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