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Synthesis of Key Intermediate of Phosphonosulfonates (BPH-652), 1-(3-Iodopropyl)-3-Phenoxy Benzene
Corresponding Author(s) : Defeng Xu
Asian Journal of Chemistry,
Vol. 26 No. 22 (2014): Vol 26 Issue 22
Abstract
A convenient and efficient four-step synthesis of 1-(3-iodopropyl)-3-phenoxy benzene can be achieved by 3-phenoxybenzaldehyde and malonic acid in the presence of piperidine and pyridine to yield (E)-3-(3-phenoxyphenyl)-2-propenoic acid, esterification with methanol in the present of p-toluene sulfonic acid, reduction with sodium borohydride to give 3-(3-phenoxyphenyl)propan-1-ol and iodination of 3-(3-phenoxy phenyl) propan-1-ol using iodine and triphenylphosphine in the present of potassium iodide and imidazole and to afford the title compound in an overall yield of 55.6 %.
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- Y.C. Song, C.I. Liu, F.Y. Lin, J.H. No, M. Hensler, Y.L. Liu, W.Y. Jeng, J. Low, G.Y. Liu, V. Nizet, A.H.J. Wang and E. Oldfield, J. Med. Chem., 52, 3869 (2009); doi:10.1021/jm9001764.
- D.R. Magnin, S.A. Biller, J.J.K. Dickson, R.M. Lawrence and R.B. Sulsky, US Patent 5,470,845 (1995).
- Y. Song, F.-Y. Lin, F. Yin, M. Hensler, C.A. Rodrígues Poveda, D. Mukkamala, R. Cao, H. Wang, C.T. Morita, D. González Pacanowska, V. Nizet and E. Oldfield, J. Med. Chem., 52, 976 (2009); doi:10.1021/jm801023u.
- T.T.W. Cheng and M.A. Poss, US 5618964 (A) (1997).
- E. Oldfield and Y.C. Song, PCT Int. Appl., WO 2010123599 A2 20101028 (2010).
- E. Oldfield and Y.C. Song, US Appl., 2012022024 (A1) (2012).
References
Y.C. Song, C.I. Liu, F.Y. Lin, J.H. No, M. Hensler, Y.L. Liu, W.Y. Jeng, J. Low, G.Y. Liu, V. Nizet, A.H.J. Wang and E. Oldfield, J. Med. Chem., 52, 3869 (2009); doi:10.1021/jm9001764.
D.R. Magnin, S.A. Biller, J.J.K. Dickson, R.M. Lawrence and R.B. Sulsky, US Patent 5,470,845 (1995).
Y. Song, F.-Y. Lin, F. Yin, M. Hensler, C.A. Rodrígues Poveda, D. Mukkamala, R. Cao, H. Wang, C.T. Morita, D. González Pacanowska, V. Nizet and E. Oldfield, J. Med. Chem., 52, 976 (2009); doi:10.1021/jm801023u.
T.T.W. Cheng and M.A. Poss, US 5618964 (A) (1997).
E. Oldfield and Y.C. Song, PCT Int. Appl., WO 2010123599 A2 20101028 (2010).
E. Oldfield and Y.C. Song, US Appl., 2012022024 (A1) (2012).