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Synthesis method of 5-bromo-2, 2-dimethyl-5-(4-methylsulfonylphenyl) furan-3 (2H)-one

The technology of a methanesulfonyl phenyl group and a synthesis method, which is applied in the field of organic synthesis, can solve the problems of large residual fluctuation of reaction raw materials, unsuitable for industrial production, etc., and achieves the effects of avoiding the acid waste water of chromium, easy industrial production, and low environmental protection pressure.

Active Publication Date: 2020-06-19
XIAN RUILIAN NEW MATERIAL CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In the first step of the above route, the remaining fluctuations of raw materials are large, and the fluctuation range of the remaining amount is 2% to 30%; the second step uses Jones reagent or MnO 2 Oxidation will produce a large amount of acidic wastewater containing heavy metal ions or heavy metal waste solids; the third step uses an organic base to close the ring, resulting in a large amount of nitrogen-containing wastewater; therefore, this method is not suitable for industrial production

Method used

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  • Synthesis method of 5-bromo-2, 2-dimethyl-5-(4-methylsulfonylphenyl) furan-3 (2H)-one
  • Synthesis method of 5-bromo-2, 2-dimethyl-5-(4-methylsulfonylphenyl) furan-3 (2H)-one
  • Synthesis method of 5-bromo-2, 2-dimethyl-5-(4-methylsulfonylphenyl) furan-3 (2H)-one

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preparation example Construction

[0035] The present invention provides a method for synthesizing 5-bromo-2,2-dimethyl-5-(4-methanesulfonylphenyl)furan-3(2H)-one, which comprises the following steps:

[0036] S1: 4-Methylthiobenzaldehyde and [(1,1-dimethyl-2-propynyl)oxy]trimethylsilane undergo a nucleophilic addition reaction under the action of n-butyl lithium to form Compound of formula (I);

[0037] S2: S1 compound of formula (I) reacts with Oxone and o-iodobenzoic acid to produce compound of formula (II);

[0038] S3: S2 compound of formula (II) undergoes ring-closing reaction under the catalysis of sulfuric acid to produce compound of formula (III);

[0039] S4: The compound of formula (Ⅲ) of S3 reacts with NBS to produce 5-bromo-2,2-dimethyl-5-[4-(methylsulfonyl)phenyl]furan-3(2H)-one ;

[0040] The synthetic route is as follows:

[0041]

Embodiment 1

[0043] A method for synthesizing 5-bromo-2,2-dimethyl-5-(4-methanesulfonylphenyl)furan-3(2H)-one, which specifically includes the following steps:

[0044] Step 1. Synthesis of the compound of formula (I):

[0045] Under the protection of nitrogen (500mL / min), add [(1,1-dimethyl-2-propynyl) to a 5000mL three-necked flask equipped with mechanical stirring, thermometer, Y-shaped tube, and 500mL constant pressure dropping funnel. 185.60g of oxy]trimethylsilane, 1L of tetrahydrofuran, after stirring for 10min, slowly lower the temperature to -90℃, start to add 594.5mL of n-butyllithium dropwise, after stirring for 1h at -90℃, add dropwise configuration to the reaction system After adding 124.81g of 4-methylthiobenzaldehyde and 124mL of tetrahydrofuran, the reaction was stopped after stirring at -90℃ for 2h. The reaction solution was slowly poured into aqueous hydrochloric acid (concentrated hydrochloric acid: 187.2mL, water: 324.5mL ), stir for 1 hour and then separate, collect the or...

Embodiment 2

[0053] A method for synthesizing 5-bromo-2,2-dimethyl-5-(4-methanesulfonylphenyl)furan-3(2H)-one, which specifically includes the following steps:

[0054] Step 1. Synthesis of the compound of formula (I):

[0055] Under the protection of nitrogen (500mL / min), add [(1,1-dimethyl-2-propynyl) to a 5000mL three-necked flask equipped with mechanical stirring, thermometer, Y-shaped tube, and 500mL constant pressure dropping funnel. 185.60g of oxy]trimethylsilane, 876mL of tetrahydrofuran, after stirring for 10min, slowly decrease the temperature to -70℃, start to add 594.5mL of n-butyllithium dropwise, after stirring at -70℃ for 1h, add dropwise configuration to the reaction system After adding 124.81g of 4-methylthiobenzaldehyde and 124mL of tetrahydrofuran, the reaction was stopped after stirring at -70℃ for 2h. The reaction solution was slowly poured into aqueous hydrochloric acid (concentrated hydrochloric acid: 187.2mL, water: 324.5mL ), stir for 1h and then separate, collect the ...

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Abstract

The invention discloses a synthesis method of 5-bromo-2, 2-dimethyl-5-(4-methylsulfonylphenyl) furan-3 (2H)-one, which belongs to the technical field of organic synthesis, and comprises the followingsteps: reacting 4-methylthiobenzaldehyde with a lithium salt of [(1, 1-dimethyl-2-propynyl) oxy] trimethylsilane to generate a compound shown in a formula (I); carrying out oxidation reaction on the compound shown in the formula (I), Oxone and o-iodobenzoic acid to generate a compound shown in a formula (II); reacting the compound shown in the formula (II) with sulfuric acid to generate a compoundshown in a formula (III); and reacting the compound shown in the formula (III) with NBS to obtain a target product. The method has the advantages of simple raw materials, low price, simple operation,short production period, no generation of chromium acidic wastewater, nitrogen-containing wastewater and the like, small environmental protection pressure, and easy realization of industrial production.

Description

Technical field [0001] The invention belongs to the technical field of organic synthesis, and specifically relates to a method for synthesizing 5-bromo-2,2-dimethyl-5-(4-methanesulfonylphenyl)furan-3(2H)-one. Background technique [0002] As we all know, prostaglandins play an important role in inflammation. Prostaglandins are produced by arachidonic acid catalyzed by cyclooxygenase. By inhibiting cyclooxygenase, the synthesis of prostaglandins can be inhibited to achieve the treatment of inflammation. There are at least two cyclooxygenases used to catalyze the production of prostaglandins: cyclooxygenase-1 (abbreviated as COX-1) and cyclooxygenase-2 (abbreviated as COX-2); 4,5-diaryl- 3(2H)-furanone derivatives can be used as COX-2 inhibitors, including 5-bromo-2,2-dimethyl-5-(4-methylsulfonylphenyl)furan-3(2H)-one . The current synthetic route of 5-bromo-2,2-dimethyl-5-(4-methylsulfonylphenyl)furan-3(2H)-one is as follows (Journal of Medicinal Chemistry, 47(4), 792-804 ,2004...

Claims

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Application Information

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IPC IPC(8): C07D307/58
CPCC07D307/58
Inventor 谌聪付青何汉江王小伟
Owner XIAN RUILIAN NEW MATERIAL CO LTD
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