Application of sulfonyl type compounds as chlorination reagent

Abstract

The invention discloses an application of a sulfonyl type compound as a chlorination reagent. The structural formula of the sulfonyl type compound is shown as the following formula (I); in formula (I), the R is a substituted or unsubstituted linear or branched alkyl group with 1 to 30 carbon atoms, which means that the alkyl group can be substituted by halogen, alkoxy with 1 to 20 carbon atoms andaryl with 6 to 14 carbon atoms, and the aryl with 6 to 14 carbon atoms can be further substituted by alkyl with 1 to 20 carbon atoms, alkoxy with 1 to 20 carbon atoms and halogen. The sulfonyl compound can perform single chlorination on carbonyl alpha-sites of organic molecules such as aldehyde, ketone, esters and the like with high selectivity under mild conditions; so that the compound can solve the safety problem of existing chlorination reagents such as chlorine, sulfonyl chloride and the like in the use process, reduces post-treatment and three-waste treatment steps, and is suitable forindustrial-scale production.

Description

technical field [0001] The invention relates to the field of fine organic synthesis, in particular to the application of a class of sulfonyl compounds as chlorination reagents. Background technique [0002] Carbonyl compounds substituted at the α-position can obtain intermediates and products with different structures and functions through reactions such as substitution, coupling, and elimination, and are widely used in the fields of organic synthesis, pharmaceuticals, and agricultural chemicals research and development, and production (Xu Guanyu Editor-in-Chief, "Handbook of Pharmaceutical Intermediates", Chemical Industry Press, 2000; Editor-in-Chief Xue Zhenxiang, "Handbook of Pesticide Intermediates", Chemical Industry Press, 2004). At present, the commonly used chlorination methods still have disadvantages such as poor stability, inconvenient operation, many by-products, high equipment requirements, and difficult handling of reactants. Therefore, it is necessary to imp...

AI Technical Summary

Problems solved by technology

These systems have disadvantages such as expensive reagents, large amounts, and potential explosion risks to varying degrees.

[0005] In 2015, the Chinese invention patent CN104610100A disclosed a nitrogen-chlorine type chlorination reagent, which partially overcomes the above shortcomings. However, due to the continuous use of fluorine gas and chlorine gas in the preparation process of the chlorination reagent, the operation is relatively inconvenient, and industrial applications are also not utilized.

[0007] There are also reports that the reactor has been improved to improve the efficiency of conventional chlorination reagents. For example, Chinese invention patent CN105384617A discloses a process for chlorination using a microreactor. The chlorination reagent is chlorine gas. Compared with traditional methods, the yield Increased by about 20-30%. Although the efficiency is improved, the chlorination reagent is chlorine gas, and there is still a certain risk of toxicity

[0008] In summary, the chlorination reagents used for carbonyl α-position have problems such as inconvenient operation, toxicity, and explosive risk, and there are problems of high raw material costs and high requirements for corrosion resistance of equipment, which is not conducive to the requirements of industrial production.

Images