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Preparation method of triketone compound and triketone compound intermediate

A technology of compounds and triketones, which is applied in the field of preparation of triketone compounds and their intermediates, can solve problems such as unfavorable industrial production, and achieve the effects of high product quality, simple process, and mild reaction conditions

Active Publication Date: 2016-06-29
ZHEJIANG ZHUJI UNITED CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This method will use highly toxic cyanide, which will produce a large amount of cyanide-containing wastewater, which is not conducive to industrial production.

Method used

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  • Preparation method of triketone compound and triketone compound intermediate
  • Preparation method of triketone compound and triketone compound intermediate
  • Preparation method of triketone compound and triketone compound intermediate

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preparation example Construction

[0033] A preparation method for triketones, comprising the steps of:

[0034] Step 1, in a solvent and in the presence of a base, react compound (I) and compound (II) at a certain temperature, and then continue to react with an oxidant to obtain compound (III);

[0035] Step 2, compound (III) is reacted with an acid chloride reagent to obtain compound (IV);

[0036] Step 3, under the action of an acid-binding agent, compound (IV) undergoes an esterification reaction with 1,3-cyclohexanedione to obtain compound (V);

[0037] Step 4, under the action of the catalyst, the compound (V) is rearranged to obtain the triketone target compound (VI);

[0038] The reaction formula is expressed as follows:

[0039]

[0040] Wherein, X is halogen, sulfonyl or sulfinyl, R is C1-C6 alkyl or C6-C10 aryl, R 1 is alkoxy, amino, alkylamino, alkyl, aryl or hydrogen.

[0041] Said X is preferably fluorine, chlorine or bromine; said R is preferably methyl; said R 1It is preferably methoxy, ...

Embodiment 1

[0049] Embodiment 1: Preparation of 2-nitro-4-methylsulfonylbenzoic acid

[0050] In a 1000mL three-necked flask, add 400mL DMSO, 53g sodium hydroxide, 66.4g methyl cyanoacetate and 150g 2-nitro-4-methylsulfonylchlorobenzene, control the temperature of the reactant within 60°C, and stir for 1 hour. Then add 124g 35% H 2 o 2 , reacted for 2 hours, quenched hydrogen peroxide, distilled and recovered DMSO, added water, acidified with hydrochloric acid, solid precipitated, filtered, and the filter cake was dried to obtain 148.6g of 2-nitro-4-methylsulfonylbenzoic acid. 1 H-NMRδppm (DMSO-d6) 14.42 (br, 1H), 8.53 (d, J = 1.6Hz, 1H), 8.33 (dd, J1 = 1.6Hz J2 = 8.0Hz, 1H), 8.12 (d, J = 8.0Hz , 1H), 3.39(s, 3H).

Embodiment 2

[0051] Embodiment 2: Preparation of 2-nitro-4-methylsulfonylbenzoic acid

[0052] In a 1000mL three-necked flask, add 400mL NMP, 128g triethylamine, 55g cyanoacetamide and 149g 2-nitro-4-trifluoromethylchlorobenzene, control the temperature of the reactant at 30°C, and stir for 2 hours. Then add 162g 40% H 2 o 2 , reacted for 2 hours, quenched hydrogen peroxide, recovered NMP by distillation, added water, acidified with hydrochloric acid, solid precipitated, filtered, and the filter cake was dried to obtain 151g of 2-nitro-4-methylsulfonylbenzoic acid.

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Abstract

The present invention discloses a preparation method of a triketone compound and a triketone compound intermediate. The method is as follows: a compound (III) is obtained by nucleophilic substitution reaction of a compound (I) as a raw material and a compound (II) under the action of a base and then oxidation reaction, and the triketone desired product is obtained by acyl chlorination, esterification and rearrangement of the compound (III). The beneficial effects are mainly reflected as follows: the method is mild in reaction conditions, simple in process, high in yield, good in product quality, low in production costs, less in three-waste, and suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a preparation method of triketone compounds and intermediates thereof. Background technique [0002] Triketones are an important class of organic intermediates, widely used in the fields of medicine and pesticides. For example, mesotrione is a triketone herbicide developed by Syngenta of Switzerland. It was registered in Europe in 2000 and began to be sold in Germany and Austria in 2001. Because of its environmental friendliness, it passed the environmental protection approval of the United States in the same year. Its single agent and mixed preparations were sold in EU countries and the United States in 2002. Mesotrione has wide application value and market prospect in the field of plant protection due to its broad herbicidal spectrum, high activity, flexible use, and strong environmental compatibility. [0003] At present, the method for industrialized preparation...

Claims

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Application Information

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IPC IPC(8): C07C317/24C07C317/44C07C315/04
Inventor 苏叶华史界平陆建鑫张天浩刘伟平蔡国平虞小华陈邦池
Owner ZHEJIANG ZHUJI UNITED CHEM
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