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A kind of improved process method for preparing 5-chlorindanone

A technology of chlorindanone and process improvement, applied in the field of organic synthesis, can solve the problems such as no public refining method, and achieve the effects of shortening production time, reducing dosage, and good product color

Active Publication Date: 2022-07-08
上海鼎素精细化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0012] The patent does not disclose the refining method. The applicant tried to dissolve, separate the tar and decolorize the activated carbon, and the obtained product is still yellow or light yellow powder. After dissolving the product, there is still a small amount of black tar substance

Method used

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  • A kind of improved process method for preparing 5-chlorindanone
  • A kind of improved process method for preparing 5-chlorindanone
  • A kind of improved process method for preparing 5-chlorindanone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Embodiment 1 (traditional process)

[0036]

[0037] Put 225g (2.0mol, 1eq) of chlorobenzene into the reaction flask, cool down to 25-30°C, add 333g (2.5mol, 1.25eq) of aluminum trichloride under stirring, and slowly add dropwise at a temperature of 25-30°C 254g (2.0mol, 1eq) of 3-chloropropionyl chloride was added dropwise and kept for 3 hours. 466.7 g (3.5 mol, 1.75 eq) of aluminum trichloride, 163 g of sodium chloride and 23.3 g of potassium chloride were added to the molten state, and heated to 135° C. to react for 4 h. Sampling HPLC to detect no intermediate remaining, the reaction solution was added to 3700g of ice water for hydrolysis, filtered and dried to obtain 330g of black solid, which was added to 1000mL of methanol to dissolve and refluxed, hot filtered, the filtrate was heated to reflux again, 30g of activated carbon was added, hot filtered, and the filtrate was Cooling and crystallization yielded 242.9 g of yellow solid, yield 72.9%, HPLC 99.1%. 1 H...

Embodiment 2

[0038] Embodiment 2 (traditional process)

[0039]

[0040] Put 227.4g (2.02mol, 1.01eq) of chlorobenzene into the reaction flask, cool down to 25-30°C, add 314.7g (2.36mol, 1.18eq) of aluminum trichloride under stirring, and control the dropwise temperature after stirring for 10 minutes Slowly add 254g (2.0mol, 1eq) of 3-chloropropionyl chloride dropwise at 25-45°C, and heat to 70-80°C for 2 hours after the dropwise addition. Sampling GC detection raw material 3-chloropropionyl chloride remaining 0.5%. It was added to 514.7g (3.86mol, 1.93eq) of aluminum trichloride and 57.3g (0.98mol, 0.49eq) of sodium chloride in a molten state, and heated to 150-165° C. to react for 3h. Sampling was detected by HPLC and no intermediate remained. After the incubation, the temperature was lowered to 105-110 ° C. The reaction solution was added to 3700 g of ice water for hydrolysis, filtered and dried to obtain 330 g of black solid. The crude product 330 g was divided into 3 parts. First, ...

Embodiment 3

[0042]

[0043] Put 227.4g (2.02mol, 1.01eq) of chlorobenzene into the reaction flask, cool down to 25-30°C, add 314.7g (2.36mol, 1.18eq) of aluminum trichloride under stirring, and control the dropwise temperature after stirring for 10 minutes Slowly add 254g (2.0mol, 1eq) of 3-chloropropionyl chloride dropwise at 25-45°C, and heat to 70-80°C for 2 hours after the dropwise addition. Sampling GC detection raw material 3-chloropropionyl chloride remaining 0.5%. It was added to 514.7g (3.86mol, 1.93eq) of aluminum trichloride and 57.3g (0.98mol, 0.49eq) of sodium chloride in a molten state, and heated to 150-165° C. to react for 3h. Sampling was detected by HPLC and no intermediate remained. After the incubation, the temperature was lowered to 105-110° C. and added dropwise to 2000 g of 4% hydrochloric acid prepared in advance. The dropwise temperature was controlled at 90-95° C., stirred for 10 minutes, allowed to stand for 30 minutes, and the lower organic layer was separa...

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Abstract

The invention discloses an improved process method for preparing 5-chlorindanone, and belongs to the technical field of organic synthesis. Chlorobenzene is mixed with anhydrous aluminum trichloride, and 3-chloropropionyl chloride is added to carry out the Friedel-Crafts acylation reaction to obtain 3,4'-dichloropropiophenone, then in anhydrous aluminum chloride / sodium chloride or tri( Under the condition of pentafluorophenyl) borane, the catalyzed ring is closed, and the 5-chlorindanone is obtained by direct rectification after the reaction finishes washing with water. The process of the invention directly distills after washing with water, without subsequent operations, reduces operation steps, shortens production man-hours, saves production costs, greatly improves the extraction effect of products, and increases the yield of products by more than 15%. It can be effectively removed, and the content of the product is increased to more than 99.5%. At the same time, the use of tris(pentafluorophenyl)borane to catalyze the ring closure can reduce the total amount of aluminum trichloride, reduce the ring closure reaction temperature, and reduce the generation of tar. , improving the yield of the product.

Description

technical field [0001] The invention relates to an improved process method for preparing 5-chloroindanone, and belongs to the technical field of organic synthesis. Background technique [0002] 5-Chloroindanone, CAS: 42348-86-7, English name: 5-Chloro-1-indanone. 5-Chlorindanone is an important biopharmaceutical intermediate, pesticide intermediate and an important intermediate for preparing metallocene complexes. Among them, 5-chlorindanone is an important heavy intermediate of indoxacarb as the parent nucleus. [0003] Indoxacarb is a carbamate insecticide developed by DuPont in 1992 and registered in 2001. Its generic name is Indoxacarb and its trade name is Vatar. Its chemical structure is as follows: [0004] [0005] Different from traditional carbamate insecticides, indoxacarb is a sodium ion channel inhibitor. It mainly blocks the sodium ion channels in the nerve cells of the pests, causing the nerve cells to lose their function, resulting in paralysis and poor...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C45/61C07C49/697C07C45/46C07C49/80
CPCC07C45/61C07C45/46C07C2602/08C07C49/697C07C49/80Y02P20/584
Inventor 李军
Owner 上海鼎素精细化工有限公司
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