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A Facile Synthesis of 3-(Chloromethyl)-2-methyl-1,1′-biphenyl
Corresponding Author(s) : Hang Hu
Asian Journal of Chemistry,
Vol. 31 No. 12 (2019): Vol 31 Issue 12
Abstract
3-(Chloromethyl)-2-methyl-1,1′-biphenyl is a key intermediate for the preparation of bifenthrin, an insecticide which belongs to pyrethroid. The traditional synthetic process of 3-(chloromethyl)-2-methyl-1,1′-biphenyl is complicated and involves high-toxic and high-risk reagents such as thionyl chloride, lithium aluminum hydride and methyl iodide, which causes significant environmental problems and safety issues. Herein, a facile and efficient synthesis process of 3-(chloromethyl)-2- methyl-1,1′-biphenyl was developed. The synthetic process is shortened from 6 steps to only 4 steps and avoids the use of high-toxic and high-risk reagents. Moreover, 3-(chloromethyl)-2-methyl-1,1′-biphenyl can be obtained by simple purification process in high yield (73.9 %). Compared with the traditional synthetic process, the synthetic process of 3-(chloromethyl)-2-methyl-1,1′-biphenyl reported here is more environmental friendly and efficient.
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- J.E. Casida, Environ. Health Perspect., 34, 189 (1980); https://doi.org/10.1289/ehp.8034189.
- J.-M. Hougard, S. Duchon, M. Zaim and P. Guillet, J. Med. Entomol., 39, 526 (2002); https://doi.org/10.1603/0022-2585-39.3.526.
- D.G. James, K. O’Malley and M. Rayner, Exp. Appl. Acarol., 19, 647 (1995); https://doi.org/10.1007/BF00145253.
- R.E. Montgomery, E.L. Plummer and A.J. Martinez, Pyrethroid Inter-mediates and Process, US Patent 4473709A (1984).
- R.F. Nystrom and W.G. Brown, J. Am. Chem. Soc., 69, 1197 (1947); https://doi.org/10.1021/ja01197a060.
- M. Selva and A. Perosa, Green Chem., 10, 457 (2008); https://doi.org/10.1039/b713985c.
- P.L. Türtscher, H.J. Davis and R.J. Phipps, Synthesis, 50, 793 (2018); https://doi.org/10.1055/s-0036-1588548.
- M. Hans and K. Frank, Process for the Preparation of Aromatic (bromo-alkyl)-substituted Hydrocarbon Compounds, DE 19547249A1 (1997).
- X. Cheng, L. Zhang, L. Chen, Q. Sun, J. Liu, Z. Li, J. Zhao, J. Xu and H. Wu, Malononitrile Oxime Ether Compound and Use thereof, WO Patent 2017107939 (A1) (2017).
- R.W. Lin, WO Patent 0144147(A1) (2001).
References
J.E. Casida, Environ. Health Perspect., 34, 189 (1980); https://doi.org/10.1289/ehp.8034189.
J.-M. Hougard, S. Duchon, M. Zaim and P. Guillet, J. Med. Entomol., 39, 526 (2002); https://doi.org/10.1603/0022-2585-39.3.526.
D.G. James, K. O’Malley and M. Rayner, Exp. Appl. Acarol., 19, 647 (1995); https://doi.org/10.1007/BF00145253.
R.E. Montgomery, E.L. Plummer and A.J. Martinez, Pyrethroid Inter-mediates and Process, US Patent 4473709A (1984).
R.F. Nystrom and W.G. Brown, J. Am. Chem. Soc., 69, 1197 (1947); https://doi.org/10.1021/ja01197a060.
M. Selva and A. Perosa, Green Chem., 10, 457 (2008); https://doi.org/10.1039/b713985c.
P.L. Türtscher, H.J. Davis and R.J. Phipps, Synthesis, 50, 793 (2018); https://doi.org/10.1055/s-0036-1588548.
M. Hans and K. Frank, Process for the Preparation of Aromatic (bromo-alkyl)-substituted Hydrocarbon Compounds, DE 19547249A1 (1997).
X. Cheng, L. Zhang, L. Chen, Q. Sun, J. Liu, Z. Li, J. Zhao, J. Xu and H. Wu, Malononitrile Oxime Ether Compound and Use thereof, WO Patent 2017107939 (A1) (2017).
R.W. Lin, WO Patent 0144147(A1) (2001).