[Fe]-t-BuOCl- a new efficient catalytic system for chlorination of arenes

Chlorine derivatives of aromatic compounds are widely used in organic chemistry as intermediates for the synthesis of pharmaceuticals. Despite the abundance of various chlorination methods, almost no workon the chlorination of organic compounds using tert-butyl hypochlorite in the presence of catalysts. We have developed a new iron-catalyzed method for chlorination of aromatic compounds using tert-butyl hypochlorite. The reactions take place with high conversion and selectivity. A new method for the chlorination of ethylbenzene and toluene with tert-butyl hypochlorite under the action of iron-containing catalysts to give 1-(chloroethyl)benzene and benzyl chloride in more than 50% yield wasdeveloped. A new iron-catalyzed method for the synthesis of 1,4-dichloro-2,3,5,6-tetramethylbenzene in 100% yield by chlorination of durene with tert-butyl hypochlorite was proposed. A method was developed for the synthesis of phenol and its derivatives (anisole and 4-nitrophenol) with the use of tert-butyl hypochlorite under the action of iron-containing catalysts with a quantitative yield of the reaction products. The developed methodology paves the way for the industrial use of the environmentally friendly reagent in the production of chlorine derivatives of aromatic compounds.