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Preparation method of nitrophenylacetonitrile compound

A technology for o-nitrobenzonitrile and compound, which is applied in the field of preparation of o-nitrobenzonitrile compounds, can solve the problems of low price, low reaction yield of ferrocyanide, low toxicity of cyanide reagent, etc. The price of raw materials, the effect of promoting industrial production and expanding the scope of use

Active Publication Date: 2014-02-19
NUTRICHEM LAB CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] The purpose of the present invention is to overcome the defect of low reaction yield of o-nitrochlorobenzene compounds and ferrocyanide in the prior art, to provide a reactant with low price, easy to buy, low toxicity of cyanide reagent, suitable for industrialization Large-scale production, and the preparation method of o-nitrobenzonitrile compound with higher product yield

Method used

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  • Preparation method of nitrophenylacetonitrile compound
  • Preparation method of nitrophenylacetonitrile compound
  • Preparation method of nitrophenylacetonitrile compound

Examples

Experimental program
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Effect test

Embodiment 1

[0035] Preparation of 2-nitro-4-trifluoromethylbenzonitrile

[0036] Under the protection of dry nitrogen, add N-methylpyrrolidone (130g), 3-nitro-4-chlorobenzotrifluoride (0.1mol), cuprous chloride (0.05mol), bromide Copper (0.01mol) and anhydrous potassium ferrocyanide (0.02mol) were stirred, heated to 160°C, and stirred for 8 hours. Subsequently, the temperature was lowered to room temperature under the protection of nitrogen, and samples were taken for GC-MS analysis. The analysis results are: the reaction conversion rate is 95.1%, and the reaction selectivity is 91%. Add 600ml of diethyl ether and 150ml of water, stir, separate the organic phase, continue to extract the water phase with diethyl ether, combine the organic phases, dry over anhydrous sodium sulfate, decolorize with activated carbon, and remove the solvent to obtain 18.2g of a yellow solid with a yield of about 84%. The mass spectral data (EI) of 2-nitro-4-trifluoromethylbenzonitrile is: 216(M+)197(M-F)186(...

Embodiment 2

[0056] Preparation of 2-nitro-4-trifluoromethylbenzonitrile

[0057]Under the protection of dry nitrogen, N,N-dimethylacetamide (130g), 3-nitro-4-chlorobenzotrifluoride (0.1mol), cuprous chloride (0.06mol) were added to the reaction flask successively , cuprous bromide (0.03mol), and anhydrous sodium ferrocyanide (0.02mol) were stirred, heated to 170°C, and stirred for 8 hours. Subsequently, the temperature was lowered to room temperature under the protection of nitrogen, and samples were taken for GC-MS analysis. The analysis results are: the reaction conversion rate is 97%, and the reaction selectivity is 93%. Add 600ml of diethyl ether and 150ml of water, stir, separate the organic phase, continue to extract the water phase with diethyl ether, combine the organic phases, dry over anhydrous sodium sulfate, decolorize with activated carbon, and precipitate 18.6g of a yellow solid with a yield of about 86%.

Embodiment 3

[0059] Preparation of 2-nitro-4-trifluoromethylbenzonitrile

[0060] Under the protection of dry nitrogen, N-methylpyrrolidone (130g), 3-nitro-4-chlorobenzotrifluoride (0.1mol), cuprous chloride (0.05mol), bromide Copper (0.02mol) and anhydrous potassium ferrocyanide (0.02mol) were stirred, heated to 170°C, and stirred for 8 hours. Subsequently, the temperature was lowered to room temperature under the protection of nitrogen, and samples were taken for GC-MS analysis. The analysis results are: the reaction conversion rate is 97.4%, and the reaction selectivity is 92.1%. Add 600ml of diethyl ether and 150ml of water, stir, separate the organic phase, continue to extract the water phase with diethyl ether, combine the organic phases, dry over anhydrous sodium sulfate, decolorize with activated carbon, and precipitate 19.2g of a yellow solid with a yield of about 89%.

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Abstract

The invention discloses a preparation method of a nitrophenylacetonitrile compound. The nitrophenylacetonitrile compound is shown as a structural formula (1), wherein R1 refers to hydrogen, alkyl with 1-6 carbon atoms or halogenated alkyl with 1-3 carbon atoms; and R2 refers to hydrogen or alkoxyl with 1-6 carbon atoms. The method comprises the following step of: reacting the compound shown as a structural formula (2) with ferrous iron cyanide salt in a solvent under the action of cuprous chloride and / or cuprous bromide serving as a catalyst under a heating condition, wherein the definitions of R1 and R2 in the formula (2) are the same as those of R1 and R2 in the formula (2). Due to the adoption of the method for preparing nitrophenylacetonitrile by taking an o-nitrochlorobenzene compound as an initiator, the toxicity of a cyanidation reaction and the cost of a reactant can be lowered; meanwhile, cuprous chloride and cuprous bromide are used in a matching way, so that an unexpected effect is achieved, the product yield can be increased, and industrial mass production is facilitated; and moreover, three wastes do not contain virulent substances, and post-treatment is easy.

Description

technical field [0001] The invention relates to a preparation method of o-nitrobenzonitrile compounds. Background technique [0002] Isoxaflutole is a hydroxyphenylpyruvate dioxygenase inhibitor. As a broad-spectrum herbicide, it is not only effective against grassy weeds such as crabgrass, barnyardgrass, giant foxtail, and foxtail, as well as velvet. Broad-leaved weeds such as hemp, purslane, quinoa, black nightshade, cocklebur, amaranth, and water spiny have very good biological activity, and are safe for corn and sugar beet crops, with little residue, and are compatible with the environment and ecology Good performance and high safety. The herbicidal mechanism of isoxamazone is as follows: by inhibiting the synthesis of p-hydroxyphenylpyruvate dioxygenase, it leads to the accumulation of tyrosine, hinders the biosynthesis of plastoquinone and tocopherol, and then affects the carotenoids of biosynthesis. The preparation method of this type of herbicide was first reporte...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C255/50C07C253/14
Inventor 赵永长陈建伟池剑鸿邓旭芳于慧梅王文军
Owner NUTRICHEM LAB CO LTD
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