Abstract
Treatment of 2,4-dinitrophenol with sulfonyl chlorides in the presence of pyridine results in the formation of undesired pyridinium salts. In non-aqueous environments, the formation of the insoluble pyridinium salt greatly affects the formation of the desired product. A facile method of producing the desired sulfonate involves the use of an aqueous base with a water-miscible solvent. Herein, we present the optimization of methods for the formation of sulfonates and its application in the production of desired x-substituted 2,4-dinitrophenyl-4′-phenylbenzenesulfonates. This strategy is environmentally benign and supports a wide range of starting materials. Additionally, the intermolecular interactions of these sulfonate compounds were investigated using single-crystal x-ray diffraction data.
Highlights
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Successful formation of the desired product occurred in all cases, except entry 8 where dichloromethane and pyridine were used. This led to the development of a new synthetic method using an aqueous base and the water-miscible solvent, tetrahydrofuran. This single-phase solvent system defeats the need for a phase transfer catalyst and can support a wider range of starting materials
Summary
AA rreelliiaabbllee mmeetthhoodd ffoorr pprroodduucciinngg aarryyllssuullffoonnaatteess iinnvvoollvveess tthhee nnuucclleeoopphhiilliicc ssuubbssttiittuuttiioonn rreeaaccttiioonn ooff aallccoohhoollss aanndd ssuullffoonnyyll hhaalliiddeess..ThTihsisreraecatciotinonisishihgihglhylyeffeifficiecnietnitnincrecaretiantgintghethseuslfuolnfoanteateesteesrt,ear, saysnythnethtiectailclaylliymipmoprtoarnttanelteectleroctprhoiplehiilne oinrgoarngicanchicemchiesmtryisdtruyedtoueitstohiigtshhcihgehmcihcaelmriecaacltirveiatcyti[v1]it.yTh[1is]. pTrhoispeprrtoypehratsy bheaesnbeuetniliuzteidliziend tihnethdeedteectteioctnioannadndfluflouroersecsecnetntimimagagininggooff bbiioollooggiiccaallllyy iimmppoorrttaanntt ccoommppoouunnddss. .e facile synthesis and characterization of x-substituted 2,4-dinitrophenyl-4′-phenylbenzenesulfonates. Evaporation of solvent yielded a solid, yellow residue as a crude product. Recrystallization in 2:1 acetone/water, followed by trituration with hexanes afforded the product as small, translucent crystalline sheets (1.875 g, 41% yield).
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