Reduction Of ?,?,?-trihalo(Br,Cl)methyl Ketones

This paper introduces a novel method of reducing?,?,?-tribromomethyl ketones with different chemical structures by using thiophenol as a reducing agent.The Na HSO₃green synthesis method of producing?,?-dibromomethyl ketones,?-monobromomethyl ketones and?,?-dichloromethyl ketones via a single primary substrate(?,?,?-tribromomethylketones)were explored.The products of the mentioned reactions such as are essential intermediates in the synthesis of pharmaceuticals,pesticides and dyes.These compounds have several industrial applications since they act as precursors for the synthesis of bioactive heterocyclic compounds.The first method involved reduction of?,?,?-tribromomethylketone compounds at room temperature in a green solvent,into?,?-dibromomethyl ketones using thiophenol as a reducing agent.Some mechanistic studies have indicated that the above-stated reaction is typically free radical type and suitable for reducing aromatic,aliphatic and heterocyclic?,?,?-tribromomethyl ketone compounds with a yield as high as 97%.Further,when Na HSO₃was added to Ethanol/H₂O solvent mix as a reducing agent,?-monobromomethyl ketone and?,?-dibromomethyl ketone compoundscould be conveniently sysnthesized even at room temperature.In the experiment,the gram reaction was carried out,and the post-treatment was simple,which was of great significance for industrial synthesis.This method is unique in that various compounds were synthesized from a single substrate only by controlling solvent parameters.Following the unique methodology explained above,the reduction of?,?,?-trichloromethyl ketones with Na HSO₃was further explored at a higher temperature of 80°C and keeping the Ethanol/H₂O solvent ratio of 1:1 The structures of the synthesized compounds were characterized and confirmed by ¹H NMR,¹³C NMR,HR-MS.The proposed reaction is thought to offer a novel approach for the synthesis of?,?-dichloromethylketone compounds due to its simplicity and efficiency.