1179802-07-3Relevant academic research and scientific papers
Synthesis and structure of 1-chlorosulfonyl-2-(4′-nitrophenoxy)-5- methylbenzene
Silveira, Michael H.,Fronczek, Frank R.
, p. 504 - 509 (2009)
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, methyl 5, s), 7.07 (1H, H4, d, J ~8.27 Hz), 7.13 (2H, H 2′, H6′, d, J ~9.0 Hz), 7.54 (1H, H 3, d, J ~8.28 Hz), 7.87 (1H, H6, s), 8.22 (2H, H 3′, 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) A, α = 67.645(11), β = 79.735(11), γ = 87.798(10)°, V = 690.5(2) A3, Z = 2.
