Convenient synthesis of regioisomerically pure 5- and 6-functionalized xanthene dyes via SNAr reaction and comparison of their reactivity towards click reaction was written by Mori, Masaya;Fujikawa, Yuuta;Inoue, Hideshi. And the article was included in Tetrahedron in 2020.Synthetic Route of C6H5ClO2 The following contents are mentioned in the article:
In this study, we present an efficient and general strategy for the individual preparation of both isomers of 5(6)-functionalized xanthene-based fluorophores. Spectroscopic anal. of the acid-base equilibrium of 5(6)-nitro xanthene dyes has shown that they exist predominantly in the colorless spirolactone form in certain aprotic dipolar solvents. In such solvents, regioisomerically selective ipso-substitution of the nitro group by sodium azide occurs at the 6- position but not at the 5- position due to the electron-withdrawing spirolactone moiety at the para-position, relative to the nitro group. This reaction allows the separation of the isomer with the 6-azide group and the intact 5-nitro isomer. The 5-nitro group of the latter was then reduced to an amino group and subsequently converted to an azide group. This strategy enables the preparation of both the 5- and 6-functionalized isomers individually from a mixture of precursors, which is otherwise unachievable. The azide isomers were then compared in reactivity by strain-promoted azide-alkyne cycloaddition (SPAAC) with bicycle[6.1.0]non-4-yene (BCN). This study involved multiple reactions and reactants, such as 4-Chlororesorcinol (cas: 95-88-5Synthetic Route of C6H5ClO2).
4-Chlororesorcinol (cas: 95-88-5) belongs to organic chlorides. Organic chlorides can be used in production of: PVC, pesticides, chloromethane, teflon, insulators. Aryl chlorides may be prepared by the Friedel-Crafts halogenation, using chlorine and a Lewis acid catalyst.Synthetic Route of C6H5ClO2
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics