Synthesis 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 being unsuitable for industrial production, the residual fluctuation of reaction raw materials is large, and achieve the effects of easy industrial production, avoiding nitrogen-containing waste water and simple operation.

Active Publication Date: 2022-04-01
XIAN RUILIAN NEW MATERIAL CO LTD
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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

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

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preparation example Construction

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

[0036] S1: 4-methylthiobenzaldehyde and [(1,1-dimethyl-2-propynyl)oxy]trimethylsilane undergo nucleophilic addition reaction under the action of n-butyllithium to generate A compound of formula (I);

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

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

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

[0040] Its synthetic route is as follows:

[0041]

Embodiment 1

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

[0044] Step 1, the synthesis of formula (I) compound:

[0045]Under the protection of nitrogen (500mL / min), add [(1,1-dimethyl-2-propynyl) Oxygen]trimethylsilane 185.60g, tetrahydrofuran 1L, after stirring for 10min, slowly cool down to -90°C, start to add 594.5mL of n-butyllithium dropwise, after stirring at -90°C for 1h, add dropwise to the reaction system to configure 124.81g of 4-methylthiobenzaldehyde and 124mL of tetrahydrofuran were added dropwise, and the reaction was stopped after stirring at -90°C for 2h, and the reaction solution was slowly poured into aqueous hydrochloric acid (concentrated hydrochloric acid: 187.2mL, water: 324.5mL ), stirred for 1 hour, then separated the liquid, collected the organic phase, washed the organic phase with water until neutral, separated the liquid, concentrated the organic phase under norm...

Embodiment 2

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

[0054] Step 1, the synthesis of formula (I) compound:

[0055] Under the protection of nitrogen (500mL / min), add [(1,1-dimethyl-2-propynyl) Oxygen]trimethylsilane 185.60g, tetrahydrofuran 876mL, after stirring for 10min, slowly cool down to -70°C, start to add 594.5mL of n-butyllithium dropwise, after stirring at -70°C for 1h, add dropwise to the reaction system to configure 124.81g of 4-methylthiobenzaldehyde and 124mL of tetrahydrofuran were added dropwise, and the reaction was stopped after stirring at -70°C for 2h, and the reaction solution was slowly poured into aqueous hydrochloric acid (concentrated hydrochloric acid: 187.2mL, water: 324.5mL ), stirred for 1 hour, then separated the liquid, collected the organic phase, washed the organic phase with water until neutral, separated the liquid, concentrated the organic phase under ...

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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 following steps : 4-methylthiobenzaldehyde reacts with lithium salt of [(1,1-dimethyl-2-propynyl)oxy] trimethylsilane to generate formula (I) compound; formula (I) compound Oxidation reaction with Oxone and o-iodobenzoic acid generates the compound of formula (II); the compound of formula (II) reacts with sulfuric acid to generate the compound of formula (III); the compound of formula (III) reacts with NBS to obtain the target product; the present invention The raw material is simple, the price is low, the operation is simple, the production cycle is short, and the generation of chromium-acid waste water and nitrogen-containing waste water is avoided, the environmental protection pressure is small, and industrial production is easy to realize.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of 5-bromo-2,2-dimethyl-5-(4-methylsulfonylphenyl)furan-3(2H)-one. Background technique [0002] It is well known that prostaglandins play an important role in inflammation. Prostaglandins are catalyzed by arachidonic acid through cyclooxygenase. By inhibiting cyclooxygenase, the synthesis of prostaglandins can be inhibited, so as 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 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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Patent Type & Authority Patents(China)
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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