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In Situ Formed I III ‐Based Reagent for the Electrophilic ortho ‐Chlorination of Phenols and Phenol Ethers: The Use of PIFA‐AlCl 3 System
Author(s) -
Nahide Pradip D.,
Ramadoss Velayudham,
JuárezOrnelas Kevin A.,
Satkar Yuvraj,
OrtizAlvarado Rafel,
CerveraVillanueva Juan M. J.,
AlonsoCastro Ángel J.,
ZapataMorales Juan R.,
RamírezMorales Marco A.,
RuizPadilla Alan J.,
DevezeÁlvarez Martha A.,
SolorioAlvarado César R.
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701399
Subject(s) - chemistry , reagent , iodobenzene , electrophile , regioselectivity , halogenation , phenol , phenols , organic chemistry , reactivity (psychology) , chlorine , electrophilic substitution , organic synthesis , combinatorial chemistry , catalysis , medicine , alternative medicine , pathology
A new and in situ formed reagent generated by mixing PIFA {bis[(trifluoroacetoxy)iodobenzene]} and AlCl 3 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.