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A method for preparing 2-(propylthio)-3-(trifluoromethyl)phenol in a microstructure reactor

The technology of a microstructure reactor and trifluoromethyl phenol is applied in the field of preparing 2--3-phenol, a key intermediate of penoxsulam, and can solve the problems of low reaction temperature, high energy consumption, low yield and the like, To achieve the effect of improving yield and improving reaction yield

Active Publication Date: 2019-03-05
HUAIAN GUORUI CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The technical problem to be solved in the present invention is: the yield is not high in the existing technology, the reaction temperature is too low, and the energy consumption is large, and a kind of preparation 2-(propylthio)- 3-(Trifluoromethyl)phenol method

Method used

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  • A method for preparing 2-(propylthio)-3-(trifluoromethyl)phenol in a microstructure reactor
  • A method for preparing 2-(propylthio)-3-(trifluoromethyl)phenol in a microstructure reactor
  • A method for preparing 2-(propylthio)-3-(trifluoromethyl)phenol in a microstructure reactor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] (1) Synthesis of compound Ⅰ-1

[0036] m-trifluoromethylphenol is transported into microstructure reactor W1 by advection pump A1, with an inner diameter of 1mm and a flow rate of 0.2mL / min; vinyl ether and methanesulfonic acid are dissolved in toluene, and are transported into microstructure reactor W1 by advection pump A2 , the flow rate is 0.608mL / min; the two are mixed at 20°C and reacted for 0.5min before entering step (2). In step (1), the molar ratio of trifluoromethylphenol to vinyl ether and methanesulfonic acid is 1:1:0.001. Samples were taken after the reaction was completed, and analyzed by GC, the conversion rate of m-trifluoromethylphenol was 100%, and the yield of compound I-1 was 100%.

[0037] (2) Synthesis of Compound Ⅱ-1

[0038] Dissolve diisopropylamine and tetramethylethylenediamine in toluene, transport it into the microstructure reactor W2 through the advection pump A3, the inner diameter is 0.05mm, and the flow rate is 0.05mL / min, and mix with...

Embodiment 2

[0044] (1) Synthesis of compound Ⅰ-2

[0045]m-Trifluoromethylphenol is transported into the microstructure reactor W1 by the advection pump A1, the inner diameter is 1mm, and the flow rate is 0.3mL / min; In reactor W1, the flow rate is 1.0 mL / min; at 30°C, the two are mixed and reacted for 0.8 min, and then enter step (2). In step (1), the molar ratio of trifluoromethylphenol to 1-propylene ethyl ether and p-toluenesulfonic acid is 1:1.1:0.001. Samples were taken after the reaction was completed, and analyzed by GC, the conversion rate of m-trifluoromethylphenol was 100%, and the yield of compound formula I-2 was 100%.

[0046] (2) Synthesis of compound Ⅱ-2

[0047] Dissolve triethylamine and tetramethylethylenediamine in toluene, transport them into the microstructure reactor W2 through the advection pump A3, the inner diameter is 0.1mm, and the flow rate is 0.075mL / min, and mix with the reaction solution from step (1) Then mix with n-butyllithium toluene solution (1.5mol / ...

Embodiment 3

[0053] (1) Synthesis of compound Ⅰ-3

[0054] m-Trifluoromethylphenol is transported into the microstructure reactor W1 by the advection pump A1, with an inner diameter of 0.5mm and a flow rate of 3mL / min; vinyl methyl ether and trifluoroacetic acid are dissolved in toluene, and are transported into the microstructure reactor by the advection pump A2 W1, the flow rate is 9.82mL / min; mix the two at 25°C, react for 1min, and enter step (2). In step (1), the molar ratio of trifluoromethylphenol to vinyl methyl ether and trifluoroacetic acid is 1:1.2:0.005. Samples were taken after the reaction was completed, and analyzed by GC, the conversion rate of m-trifluoromethylphenol was 100%, and the yield of compound formula I-3 was 100%.

[0055] (2) Synthesis of compound Ⅱ-3

[0056] Dissolve aniline and tetramethylethylenediamine in toluene, transport it into the microstructure reactor W2 through the advection pump A3, the inner diameter is 0.5mm, and the flow rate is 8.6mL / min, mix...

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Abstract

The invention relates to the field of fine chemical engineering, in particular to a method for preparing a penoxsulam key intermediate 2-(propylthio)-3-(trifluoromethyl)phenol in a microstructural reactor. By means of the method for preparing 2-(propylthio)-3-(trifluoromethyl)phenol in the microstructural reactor, the problem in a traditional technology that feeding and purifying need to be conducted multiple times is solved, the reaction yield is increased, the problems in the traditional technology that the reaction time is long and the energy consumption is high when butyl lithium is dropwise added at an ultralow temperature are solved, the yield is greatly increased, and meanwhile, the reaction temperature is close to the room temperature and the reaction is milder.

Description

technical field [0001] The invention relates to the field of fine chemicals, in particular to a method for preparing 2-(propylthio)-3-(trifluoromethyl)phenol, a key intermediate of penoxsulam, in a microstructure reactor. Background technique [0002] Penoxsulam is a post-emergence herbicide (US5858924) developed by Dow Agro-Sciences. It is a triazolopyrimidine sulfonamide herbicide and works by inhibiting acetolactate synthase . As a broad-spectrum herbicide in paddy fields, it can effectively control barnyard grass, stephenia chinensis and annual sedge weeds, and is effective against many broad-leaved weeds, such as Heterocarpus marsh, carp sausage, turmeric, bamboo knot flower, duck Tongue grass, etc. At the same time, it can also control bensulfuron-methyl-resistant weeds in rice fields, and has residual activity against many broad-leaved and Cyperaceae weeds and barnyard grass. It is currently the species with the widest herbicidal spectrum among herbicides for rice f...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C323/20C07C319/14C07C319/20C07F1/02C07C41/14C07C43/225
CPCC07C41/14C07C319/14C07C319/20C07F1/02C07C43/225C07C323/20
Inventor 李明陈超钟钰王凤云张璞陈明光
Owner HUAIAN GUORUI CHEM CO LTD
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