2668-24-8Relevant articles and documents
In Situ Formed IIII-Based Reagent for the Electrophilic ortho-Chlorination of Phenols and Phenol Ethers: The Use of PIFA-AlCl3 System
Nahide, Pradip D.,Ramadoss, Velayudham,Juárez-Ornelas, Kevin A.,Satkar, Yuvraj,Ortiz-Alvarado, Rafel,Cervera-Villanueva, Juan M. J.,Alonso-Castro, ángel J.,Zapata-Morales, Juan R.,Ramírez-Morales, Marco A.,Ruiz-Padilla, Alan J.,Deveze-álvarez, Martha A.,Solorio-Alvarado, César R.
, p. 485 - 493 (2018/02/09)
A new and in situ formed reagent generated by mixing PIFA {bis[(trifluoroacetoxy)iodobenzene]} and AlCl3 was introduced in the organic synthesis for the direct and highly regioselective ortho-chlorination of phenols and phenol ethers. An efficient electrophilic chlorination for these electron-rich arenes as well as the scope of the reaction are described herein. An easy, practical, and open-flask reaction allowed us to introduce a chlorine atom, which is a highly important functional group in organic synthesis. The reproducibility of our method has been demonstrated on gram-scale by carrying out the reaction in 6-bromo-2-naphthol. This halogenation reaction also proceeds in excellent conditions by first preparing the iodine(III)-based chlorinating reagent. Our new chlorinating reagent can be stored at least for two weeks at 4 °C without losing its reactivity.
