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Green Chlorination of Organic Compounds Using Trichloroisocyanuric Acid(TCCA)

The present review summarizes the synthetic application of trichloroisocyanuric acid(TCCA) [1,3,5-trichloro-1,3,5-triazine-2,4,6- (1H,3H,5H)-trione] as a convenient reagent for the electrophilic chlorination of unsaturated carbon-carbon bonds and focuses on its green aspects. Chlorination reactions involving alkenes, alkynes, arenes, and (di)carbonyl compounds and the chlorodecarboxylation of cinnamic acids (Hunsdiecker reaction) are presented and discussed. Trichloroisocyanuric acid is a safe, stable, easily handled, inexpensive and commercially available solid. At the end of the reactions, cyanuric acid is obtained as by-product and can be reused to produce trichloroisocyanuric acid. In accordance with green chemistry principles, the use of trichloroisocyanuric acid enables chlorination without chlorine or other harmful or dangerous reagents.
Here we use trichloroisocyanuric acid(TCCA) as a  reagent. Nano-ZrO2 sulfuric acid [n-ZrO2–SO3H (n-ZrSA)] has been synthesized from the reaction of nano-ZrO2 with chlorosulfonic acid as sulfonating agent. This catalyst was characterized via FT-IR, XRD, TGA, FESEM, TEM, EDX, BET, BJH, ICP and pH analysis. We show that n-ZrSA catalyzed the Biginelli reaction for the synthesis of 3,4-dihydropyrimidin-2(1H)one derivatives in high yields under solvent-free conditions by the reaction of aldehyde, β-diketoester and urea (or thiourea). The main advantages of the catalyst are its non-toxic nature, high stability and reusability.
Dichlorination of 4-nitrotoluene 2 with trichloroisocyanuric acid(TCCA),   Benzoic acid 4 was reacted with thionyl chloride, followed by methanol,to afford reagent. Fluorous Yamaguchi (FY) reagents bearing a perfluoroalkyl chain were prepared and employed in esterification reactions; the yields were similar to those obtained with the traditional Yamaguchi (TY) reagent. Fluorous benzoic acids derived from the FY reagents were separated easily after the reaction. GC analysis revealed that the initial rates of reaction with the FY reagents were higher than those with the TY reagent. The acidities of benzoic acids produced from the FY and TY reagents were predicted by DFT to be similar.