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- Title
In Situ Formed I<sup>III</sup>-Based Reagent for the Electrophilic ortho-Chlorination of Phenols and Phenol Ethers: The Use of PIFA-AlCl<sub>3</sub> System.
- Authors
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.
- Abstract
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.
- Subjects
IODINE compounds synthesis; CHEMICAL reagents; PHENOLS; CHLORINATION; HALOGENATION; ELECTROPHILIC substitution reactions
- Publication
European Journal of Organic Chemistry, 2018, Vol 2018, Issue 4, p485
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201701399