Method for preparing (Z)-4-(2-bromovinyl) benzene sulfonate phenolic ester

By using the reaction of 3-(4-chlorosulfonylphenyl)-2,3-dibromopropionic acid and phenol in CH2Cl2-DMF solvent, the problem of (Z)-4-(2-bromoethylene in the prior art) is solved. It solves the stereoselectivity problem in the synthesis of phenol benzenesulfonate, realizes an efficient and environmentally friendly synthesis method, and provides important organic synthesis intermediates.

CN101544583BInactive Publication Date: 2012-05-23TONGJI UNIV
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
Filing Date
2009-05-07
Publication Date
2012-05-23
Estimated Expiration
Not applicable · inactive patent

AI Technical Summary

Technical Problem

The existing technology lacks a highly stereoselective and efficient synthesis method of (Z)-4-(2-bromovinyl)benzenesulfonate phenol ester, which limits its application in the fields of organic chemistry, biomedicine and pharmaceutical intermediates. .

Method used

Using 3-(4-chlorosulfonylphenyl)-2,3-dibromopropionic acid and phenol under the action of triethylamine, a one-pot reaction was carried out in CH2Cl2-DMF solvent, and the reaction was gradually returned to room temperature. In 10-15 hours, highly stereoselective (Z)-4-(2-bromovinyl)benzenesulfonate phenol ester was obtained.

Benefits of technology

It achieves high stereoselective synthesis, reduces the purification steps of intermediate compounds and the usage of organic solvents, has the effect of environmental protection and emission reduction, and provides important organic synthesis intermediates that are cheap and easy to obtain.

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Abstract

The invention belongs to the technical field of synthesis of medicinal intermediates, and in particular relates to a method for preparing (Z)-4-(2-bromovinyl) benzene sulfonate phenolic ester. The method comprises the following steps that: 3-(4- sulfonatophenyl)-2,3-dibromopropionic acid and phenol as raw materials and CH2C12-DFM as a mixed solvent are added with Et3N at zero temperature; and the room temperature is recovered gradually, and the mixture reacts for 10 to 15 hours to steroselectively synthesize the (Z)-4-(2-bromovinyl) benzene sulfonate phenolic ester (Z / E: more than 99 / 1) with the yield of 78.5 to 81.0 percent by a one-pot process. The (Z)-4-(2-bromovinyl) benzene sulfonate phenolic ester synthesized by the method is important organic synthesis intermediates, and can synthesize aromatic sulfone compounds with important physiological activity through reaction with a Grignard reagent. Sulphonic acid ester can be transformed into sulfonamide compounds, so the sulphonic acid ester is an important medicinal intermediate. The stereospecific (Z)-beta-bromostyrene is organic synthesis building blocks with wide application value. The intermediates are used to synthesize steroselective (Z)-olefin, and are important precursors for synthesizing alkyne. Through Stille reaction, Suzuki reaction, Sonogashira reaction, Buchwald reaction, and other metal catalytic coupling reactions, the intermediates are widely applied to synthesizing natural products and antibacterial medicaments.
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