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2-substituent-4-methylsulfonyl-alpha,alpha,alpha-trichlorotoluene, and preparation method and application thereof

A technology of thiamphenyltoluene and trichlorotoluene, which is applied in the field of triketone herbicide intermediates, achieves the effects of low cost, short process route, and less waste

Active Publication Date: 2014-03-26
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Theoretically, the compounds shown in formula (I) and formula (III) can be obtained by hydrolyzing the compound shown in formula (IV) under different conditions, however, due to the influence of substituents, the compound shown in formula (IV) Not easily obtained by common reaction methods
The compound shown in formula (IV) and its synthetic method have not been reported yet

Method used

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  • 2-substituent-4-methylsulfonyl-alpha,alpha,alpha-trichlorotoluene, and preparation method and application thereof
  • 2-substituent-4-methylsulfonyl-alpha,alpha,alpha-trichlorotoluene, and preparation method and application thereof
  • 2-substituent-4-methylsulfonyl-alpha,alpha,alpha-trichlorotoluene, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Example 1: Synthesis of 2-chloro-4-thiamphenicol-α, α, α-trichlorotoluene

[0024] Add 2-chloro-4-thiamphenicol toluene (40.9g, 0.2mol) and 205mL carbon tetrachloride into a 500mL tetrafluoro-lined autoclave, stir and dissolve at room temperature, then add sodium carbonate (63.6g, 0.6mol), and then Pass in chlorine gas (42.6g, 0.6mol), raise the temperature to 60°C and stir for 12 hours, the reaction pressure is 0.2-0.6MPa, cool to room temperature after the reaction, ventilate excess chlorine gas, take out the reaction solution, filter, add 50mL water to the filtrate and wash , layered, and the organic layer was dried with anhydrous sodium sulfate and then precipitated under reduced pressure to obtain 60.5 g of a brownish-yellow liquid. Through gas chromatography analysis, the content of 2-chloro-4-thiamphenicol-α,α,α-trichlorotoluene It was 92.3%, and the yield was 90.6%. MS(m / e): 306(76%), 308(100%), 310(47%). 1 H NMR(δ,ppm):7.96(d,J=2.0Hz,1H),7.82(dd,J=8.0Hz,2.0Hz...

Embodiment 2

[0025] Example 2: Synthesis of 2-chloro-4-thiamphenicol-α, α, α-trichlorotoluene

[0026] Add 2-chloro-4-thiamphenicol toluene (40.9 g, 0.2 mol) and 327 mL of carbon tetrachloride into a 1000 mL tetrafluoro-lined autoclave, stir and dissolve at room temperature, then add potassium carbonate (110.4 g, 0.8 mol), and then Pass in chlorine gas (56.8g, 0.8mol), raise the temperature to 80°C and stir for 8 hours, and the reaction pressure is 0.4-1.0MPa. After the reaction, cool to room temperature, ventilate excess chlorine gas, take out the reaction liquid, filter, and add 80 mL of water to the filtrate for washing , layered, and the organic layer was desolvated under reduced pressure to obtain 61.2 g of a brownish-yellow liquid. According to gas chromatography analysis, the content of 2-chloro-4-thiamphenicol-α, α, α-trichlorotoluene was 98.4%, and the yield was 97.8% %.

Embodiment 3

[0027] Example 3: Synthesis of 2-nitro-4-thiamphenicol-α, α, α-trichlorotoluene

[0028] Add 2-nitro-4-thiamphenicol toluene (43.0g, 0.2mol) and 258mL p-chlorobenzotrifluoride into a 500mL PTFE-lined autoclave, stir and dissolve at room temperature, then add sodium carbonate (74.2g, 0.7mol) , then pass in chlorine gas (49.7g, 0.7mol), heat up to 80°C and stir for 12 hours, the reaction pressure is 0.2-0.8MPa, after the reaction is completed, cool to room temperature, ventilate the excess chlorine gas, take out the reaction liquid, filter, add water to the filtrate Wash with 50 mL, separate layers, and desolvate the organic layer under reduced pressure to obtain 61.5 g of brown-yellow liquid. According to gas chromatography analysis, the content of 2-nitro-4-thiamphenicol-α,α,α-trichlorotoluene is 96.6%. The yield is 93.3%. MS(m / e): 317(100%), 319(95%), 321(30%). 1 H NMR(δ,ppm):8.34(d,J=2.0Hz,1H),8.32(dd,J=7.6Hz,2.0Hz,1H),7.99(d,J=7.6Hz,1H),3.28(s ,3H).

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Abstract

The invention discloses 2-substituent-4-methylsulfonyl-alpha,alpha,alpha-trichlorotoluene having a structure represented by formula (IV), and a preparation method and an application thereof. The preparation method comprises the following steps: adding 2-substituent-4-methylsulfonyltoluene having a structure represented by formula (II), an inert organic solvent and an acid binding agent into an autoclave, introducing chlorine, closing the autoclave, heating to 20-150DEG C for a reaction at 0.1-2MPa for 4-40h, and post-processing the obtained reaction solution after the reaction to obtain the above product (IV). The above compound (IV) can be used for synthesizing a triketone herbicide key intermediate 2-substituent-4-methylsulfonylbenzoyl chloride represented by formula (I). Compared with present 2-substituent-4-methylsulfonylbenzoyl chloride synthesis methods, the method has the advantages of short process route, few three wastes, low cost and the like.

Description

(1) Technical field [0001] The invention relates to a triketone herbicide intermediate 2-substituent-4-thiamphenyl-α,α,α-trichlorotoluene and a preparation method and application thereof. (2) Background technology [0002] Triketone herbicides mainly include Sulcotrione, Mesotrione, Tembotrione, Benzobicylon and other varieties. These herbicides are highly effective, broad-spectrum and safe. And other advantages, are widely used in farmland weeding. The synthesis of such compounds requires the use of the key intermediate 2-substituent-4-thiamphenicol benzoyl chloride, as shown in formula (I). In the following formulas (I), (II), (III) and (IV), X represents Cl or NO 2 . [0003] [0004] The synthesis of 2-substituent-4-thiamphenicol benzoyl chloride shown in formula (I) usually includes two-step reactions: first obtain 2-substituent by oxidation of 2-substituent-4-thiamphenicol toluene (formula II) -4-thiamphenicol benzoic acid (formula III), followed by acyl chlorid...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C315/04C07C317/14C07C317/44
Inventor 杜晓华徐振元
Owner ZHEJIANG UNIV OF TECH
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