1030825-20-7Relevant articles and documents
METHOD FOR PRODUCING 5-BROMO-2-ALKYLBENZOIC ACID
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Paragraph 0068; 0072-0074, (2021/09/03)
PROBLEM TO BE SOLVED: To provide a method for producing 5-bromo-2-alkylbenzoic acid, which is useful as a synthetic intermediate of a drug substance such as an antidiabetic, in an industrially inexpensive and efficient manner. SOLUTION: The present disclosure provides a method for producing 5-bromo-2-alkylbenzoic acid by bringing 2-alkylbenzoic acid and bromine into contact with each other, in the presence of sulfuric acid. Particularly if 2-alkylbenzoic acid is 2-methylbenzoic acid, the inventive production method enables efficient production of 5-bromo-2-methylbenzoic acid to be a raw material for producing canagliflozin, one of antidiabetics. SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT
Preparation method of 2-(4-fluorophenyl)-5-[(5-bromo-2-methylphenyl)methyl]thiophene
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, (2020/04/17)
The invention belongs to the field of chemistry, and particularly relates to a novel synthesis method of a key intermediate 2-(4-fluorophenyl)-5-[(5-bromo-2-methylphenyl)methyl]thiophene for preparinga medicine canagliflozin for treating type 2 diabetes mellitus. Cheap and easily available 2-methylthiophene used as an initial raw material undergoes five steps of halogenation, p-nitrotoluene alkylation, coupling, nitro reduction and a Sandmeyer reaction to prepare the product. The method has the characteristics of simplicity in operation, high reaction selectivity, few byproducts and high product quality.
Synthesis method of canagliflozin intermediate
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, (2020/02/14)
The invention discloses a synthesis method of a canagliflozin intermediate. The method comprises the following steps: 4-bromotoluene and ethyl 5-bromolevulinate which are used as initial raw materialsundergo a Friedel-Crafts reaction under the catalysis of aluminum trichloride to obtain a compound 3; the compound 3 undergo a hydrolysis reaction under an alkaline condition to obtain a compound 4;the compound 4 reacts with dimethyl sulfoxide to produce acyl chloride, and then the acyl chloride and fluorobenzene undergo the Friedel-Crafts acylation reaction under the catalysis of aluminum trichloride to obtain a compound 5; and the compound 5 is cyclized at 150-200 DEG C by adopting thiophosphoryl trisulfide to obtain 2-(4-fluorophenyl)-5-[(5-bromo-2-methylphenyl)methyl]thiophene. The synthesis method has the advantages of simple raw materials, simple operation steps, high purity and high yield of the product, and suitableness for industrial production.