223646-24-0

Basic information

• Product Name: 3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonyl-2-methylbenzoic acid
• Synonyms: 3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonyl-2-methylbenzoic acid
• CAS NO: 223646-24-0
• Molecular Weight: 283.305
• Mol File: 223646-24-0.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonyl-2-methylbenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonyl-2-methylbenzoic acid(223646-24-0)
• EPA Substance Registry System: 3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonyl-2-methylbenzoic acid(223646-24-0)

Safety Data

• Hazardous Substances Data: 223646-24-0(Hazardous Substances Data)

Upstream product

• 52331-02-9 1,4-dichloro-2,3-dimethyl-benzene 
• 95-47-6 o-xylene 
• 124-38-9 carbon dioxide 
• 66794-10-3 1,2-dimethyl-3-(methylsulfanyl)benzene 
• 247922-29-8 3-(3-bromo-2-methyl-6-(methylsulfonyl)phenyl)-4,5-dihydroisoxazole 
• 128277-66-7 2,3-dimethyl-4-methanesulfonyl-1-bromobenzene 
• 250593-00-1 2,3-dimethyl-4-methylsulfanylbromobenzene 
• 250593-01-2 2,3-dimethyl-4-methanesulfonyl-1-chlorobenzene 
• 1885-76-3 2-cyano-3-nitrotoluene 
• 74-85-1 ethene 

Downstream Products

• 223646-31-9 3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonyl-2-methylbenzoyl chloride 
• 210631-68-8 topramezone 

Relevant articles and documents

Novel compound, and method for preparing topramezone intermediate from novel compound

The invention provides a compound as shown in a general formula A. In the compound, R1 is a halogenated alkyl group, a hydroxyalkyl group, an aldehyde group or a carboxylic acid group; R2 is a methyl groupa; R3 is a cyano group, a chlorine substituted oximido group, or a 4, 5-dihydroisoxazole-3-yl group; and R4 is an alkyl substituted sulfenyl group, an alkyl sulfonyl group or an alkyl sulfoxide group, and the alkyl group is independently selected from methyl, ethyl, propyl and isopropyl. The invention also provides the compound as one or more intermediates for preparing topramezone. In addition, the invention provides a method for preparing a topramezone compound. The topramezone compound is prepared by taking the compound as shown in the general formula A as an intermediate, and the key intermediate of topramezone is finally prepared through chloromethylation or hydroformylation, hydrolysis, hydroxyamination reaction, diazotization halogenation, dipolar cycloaddition and oxidation reaction. The reaction conditions provided by the invention are mild and controllable, the reaction selectivity of each step is good, the yield is relatively high, the generation of some byproducts is avoided, and the product quality is ensured. The whole process route is easy to realize industrialization.

Topramezone intermediate and topramezone preparation method

The invention relates to the field of organic synthesis, in particular to a topramezone intermediate and a topramezone preparation method. The topramezone preparation method comprises the following steps: 3-[3-halogen-2-methyl-6-(methylsulfonyl)phenyl]-4, 5-dihydroisoxazole and cyanide are subjected to a substitution reaction to obtain 3-[3-cyano-2-methyl-6-(methylsulfonyl)phenyl]-4, 5-dihydroisoxazole; hydrolysis reaction is performed on 3-[3-cyano-2-methyl-6-(methylsulfonyl)phenyl]-4, 5-dihydroisoxazole under the action of acid or alkali to obtain 2-methyl-3-(4, 5-dihydroisoxazole-3-yl)-4-methylsulfonyl benzoic acid; and 2-methyl-3-(4, 5-dihydroisoxazole-3-yl)-4-methylsulfonyl benzoic acid and 1-methyl-5-hydroxypyrazole are condensed and rearranged to generate topramezone. According to the topramezone intermediate and the topramezone preparation method provided by the invention, the use of an expensive palladium catalyst and a dangerous butyl lithium reagent is avoided, the yield isrelatively high, the cost is reduced, the process is simplified, the defects in the prior art are overcome, and the industrial value is achieved.

Improved method for preparing topramezone

The invention discloses an improved method for preparing topramezone and belongs to the technical field of chemical synthesis. The improved method takes 3-nitro-o-xylene as a raw material and is characterized in that the topramezone is obtained through oximation reaction, ethylene cyclization, palladium carbon reduction, diazotization, aldehydelation, oxidation and condensation rearrangement reaction; under optimal conditions, the total yield is 33.7 percent, the raw material is cheap and easy to obtain, the treatment is convenient in the whole process, the yield is relatively high, and a certain significance in industrialized production is realized.