A kind of preparation method of azide compound substituted by ortho trifluoromethyl group

Abstract

The invention discloses a preparation method of an ortho-trifluoromethyl-substituted azide compound. The preparation method of the ortho-trifluoromethyl-substituted azide compound comprises the following steps of adding manganese salts, olefin derivatives, sodium trifluoromethanesulfinate, azidotrimethylsilane and a peroxy compound into a solvent in the presence of inert gas, and carrying out reaction at 25-75 DEG C for 6-12 hours; and then, carrying out column chromatography separation so as to be subjected to purifying, and obtaining the ortho-trifluoromethyl-substituted azide compound. Themole ratio of the manganese salts to the olefin derivatives to the sodium trifluoromethanesulfinate to the azidotrimethylsilane to the peroxy compound is 0.1-0.2) to 1 to (1.5-2.5) to (2.5-3.5) to (2.5-3.5); and the dosage of the solvent is 6-7 milliliters of the solvent for per millimole of the olefin derivatives. The preparation method of the ortho-trifluoromethyl-substituted azide compound is low in raw material costs, mild in reaction conditions, simple in post-treatment and suitable for industrial production.

Description

technical field [0001] The invention relates to a method for preparing an azide compound substituted by an ortho-trifluoromethyl group by trifluoromethyl-azidation of an olefin derivative. Background technique [0002] The trifluoromethyl group has a strong electron-withdrawing ability, and has the characteristics of lipophilicity, hydrophobicity, and good stability. The introduction of trifluoromethyl groups into potential candidate drug molecules can obviously adjust the physical, chemical and biological properties of these candidate drug molecules. Drug molecules containing trifluoromethyl groups play a very important role in the pharmaceutical field. Moreover, the introduction of trifluoromethyl groups into pesticide molecules such as herbicides and fungicides can also change the water solubility and biological activity of the molecules. Pesticide molecules containing trifluoromethyl groups also have important applications in the field of agrochemicals. In addition, tri...

AI Technical Summary

Problems solved by technology

[0003] The traditional step-by-step method of introducing trifluoromethyl and azide groups into organic molecules has the disadvantages of cumbersome reaction steps and low bonding efficiency. The method of difunctionalization of double bonds derived from olefins can simultaneously Introduction of trifluoromethyl and azide groups has the advantage of step economy

However, the existing trifluoromethyl-azide difunctionalization method uses Umemoto's reagent and Togni reagent, which are expensive and difficult to store, and the azide source mostly uses sodium azide, a highly toxic and explosive metal azide compound. , there are even azide reagents that require the use of hypervalent iodine that has not yet been commercialized