High-yielding Aqueous Synthetic Reactions For Chloroacetophenones And Aroyl Chlorohydrins

Recent years have seen many remarkable achievements in organic chemistry,not only enriching its contents,but also deepening the depth of its contents.Theses developments have promoted the progress in biomedical research.However,most of the current organic reactions are employing organic solvents as reaction media,which pollute the environment and add to the costs of chemical products.The aim of this research is to develop a series of aqueous reactions dealing with these problems.Herein,two such new synthetic reactions mediated by water are reported.The first one is the halogen exchange reaction of bromoacetophenone using PhSO2 Cl as chlorine source.This reaction was mediated solely by water and high-yielding.The products after extractions were pure enough that does not require further purification.This is important because the polarity of the bromoacetophenone and chloroacetophenone is very close,and it is difficult to purify the products by column chromatography or thin-layer chromatography.Fourteen such examples are presented to demonstrate the efficiency of this procedure.Another reaction converts aroyl epoxides to aroylchlorohydrins using MsCl as chlorine source in aqueous media.The optimized reaction conditions lead stereoselectively to the nearly quantitative products.Nine such examples are presented to demonstrate the efficiency of this procedure.In addition,both reactions were readily scaled up to 10 grams.The reaction mechanisms are discussed based on the control experiments.In summary,these two new reactions are high-yielding,stereoselective,operationally simple,chromatography-free and mediated by water.