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Synthesis and Structure of 1-Chlorosulfonyl-2-(4′-Nitrophenoxy)-5-Methylbenzene

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Abstract

Diphenyl ethers are structural elements found in medicinally useful antibiotics such as vancomycin as well as in biological toxins in the environment such as dioxins. The purpose of this paper is to report the synthesis and characterization of the previously unreported 1-chlorosulfonyl-2-(4′-nitrophenoxy)-5-methylbenzene, a trisubstituted diphenyl ether derivative. 1H NMR (CDCl3) δ 2.45 (3H, methyl5, s), 7.07 (1H, H4, d, J ~8.27 Hz), 7.13 (2H, H2′, H6′, d, J ~9.0 Hz), 7.54 (1H, H3, d, J ~8.28 Hz), 7.87 (1H, H6, s), 8.22 (2H, H3′, H5′, J ~9 Hz); 13C NMR (CDCl3) δ 20.7, 118.2, 121.9, 126.0, 129.8, 135.2, 135.8, 137.8, 143.8, 150.3, 161.4. An X-ray analysis has provided valuable insight into the effect of steric factors on the three dimensional shape of this compound which serves as a useful advanced intermediate in the synthesis of these biologically active molecules. A multistep synthesis of this molecule has been designed by retrosynthetic analysis as part of an ongoing program aimed at a function-oriented, multi-step economical synthesis of vancomycin lead antibiotics. Crystals are triclinic, space group P-1, a = 7.6537(15), b = 8.976(2), c = 11.050(2) Å, α = 67.645(11), β = 79.735(11), γ = 87.798(10)°, V = 690.5(2) Å3, Z = 2.

Graphical Abstract

The synthesis and characterization of the previously unreported trisubstituted diphenyl ether derivative are reported. The phenyl rings form a dihedral angle of 64.49(4)° and the chlorosulfonyl group has a C–C–S–Cl torsion angle of 62.95(11)°.

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Acknowledgments

We thank the following from LSU, Baton Rouge: Dale Traleaven and Thomas Weldeghiorghis for recording the 1H NMR and 13C NMR spectra and Anne Grove for advice and helpful discussions. The purchase of the diffractometer was made possible by grant No. LEQSF (1999–2000)-ENH-TR-13, administered by the Louisiana Board of Regents. Financial support by Our Lady of the Lake College, Baton Rouge, LA and The Board of Regents, Baton Rouge, LA in the form of Faculty Endowment Professorships (2004–2008) awarded to MHS is greatly appreciated.

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Authors and Affiliations

  1. Forensic Science Program, Department of Sciences, Our Lady of the Lake College, 5345 Brittany Drive, Baton Rouge, LA, 70808, USA

    Michael H. Silveira

  2. Department of Chemistry, Louisiana State University, Baton Rouge, LA, 70803, USA

    Frank R. Fronczek

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  1. Michael H. Silveira
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  2. Frank R. Fronczek
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Correspondence to Michael H. Silveira.

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Silveira, M.H., Fronczek, F.R. Synthesis and Structure of 1-Chlorosulfonyl-2-(4′-Nitrophenoxy)-5-Methylbenzene. J Chem Crystallogr 39, 504–509 (2009). https://doi.org/10.1007/s10870-008-9512-x

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  • DOI: https://doi.org/10.1007/s10870-008-9512-x

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