Preparing method of ortho-nitrobenzonitrile series 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 being difficult to obtain, expensive 3-nitro-4-bromotrifluorotoluene and the like, and achieves reaction selectivity And the effect of high conversion rate, shortened reaction time and simplified process operation

Active Publication Date: 2009-11-25
NUTRICHEM LAB CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Patent US4886936 provides a method for using 3-nitro-4-bromobenzotrifluoride and cuprous cyanide as raw materials to synthesize 2-nitro-4-trifluoromethylbenzonitrile.

Method used

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  • Preparing method of ortho-nitrobenzonitrile series compound
  • Preparing method of ortho-nitrobenzonitrile series compound
  • Preparing method of ortho-nitrobenzonitrile series compound

Examples

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Example Embodiment

[0024] Example 1 Preparation of 2-nitro-4-trifluoromethylbenzonitrile

[0025] Under the protection of passing through dry nitrogen, 130g of N-methylpyrrolidone, 22.6g (0.1mol) of 3-nitro-4-chlorobenzotrifluoride, 8.9g (40mmol) of nickel bromide, and cyanide were successively added to the reaction flask. Cuprous 9.0g (0.1mol). Turn on stirring, heat to 160° C., and stir for 3 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 were: the reaction conversion rate was 99.8%, and the reaction selectivity was 98.8%. Add 600mL of ether and 150mL of water, stir, separate the organic phase, extract the water phase twice with 30mL of ether, combine the organic phases, dry over sodium sulfate water and decolorize with activated carbon to obtain 19.5g of yellow solid with a yield of 90%. The mass spectral data (EI) of 2-nitro-4-trifluoromethylbenzonitrile is: 216 (M + )19...

Example Embodiment

[0026] Example 2 Preparation of 2-nitro-4-trifluoromethylbenzonitrile

[0027] Under the protection of passing through dry nitrogen, 130g of sulfolane, 22.6g (0.1mol) of 3-nitro-4-chlorobenzotrifluoride, 4.5g (20mmol) of nickel bromide, and 10.8g of cuprous cyanide were successively added to the reaction flask (0.12 mol). Turn on stirring, heat to 170°C, and stir for 5 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 were: the reaction conversion rate was 96.5%, and the reaction selectivity was 99.0%. Add 600mL of ether and 150mL of water, stir, separate the organic phase, extract the water phase twice with 30mL of ether, combine the organic phases, dry over anhydrous sodium sulfate and decolorize with activated carbon to obtain 18.8g of a yellow solid with a yield of 87%.

Example Embodiment

[0028] Example 3 Preparation of 2-nitro-4-trifluoromethylbenzonitrile

[0029] Under the protection of feeding dry nitrogen, benzonitrile 30g, 3-nitro-4-chlorobenzotrifluoride 4.5g (20mmol), nickel bromide 0.45g (2mmol), PEG-400 (poly Ethylene glycol) 30g, cuprous cyanide 2.2g (0.024mol). Start stirring, heat to 180°C, and stir for 6 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 were as follows: the reaction conversion rate was 90.5%, and the reaction selectivity was 79.0%. Add 120mL of ether and 30mL of water, stir, separate the organic phase, extract the aqueous phase twice with 10mL of ether, combine the organic phases, dry over anhydrous sodium sulfate and decolorize with activated carbon, and desolventize to obtain 2.9g of a yellow solid with a yield of 66%.

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Abstract

The present invention provides a preparing method of ortho-nitrobenzonitrile series compound, wherein, R1 and R3 are simultaneously or respectively as hydrogen, C1-C6 hydrocarbyl, C1-C3 halohydrocarbon, C1-C3 sulfenyl, C1-C3 sulfonyl, fluorine, fluorine, chlorine, bromium, nitro, R2 and R4 are simultaneously or respectively as hydrogen, C1-C6 alkoxyl, characterized in that, the ortho-nitrobenzonitrile series compound can be reacted to prepare by the compound and the cyanide of general formula (II) under the action of the catalyst nickelous bromide; wherein, the definitions of the R1-R4 groups in the general formula (II) are the same as the general formula (I), X is as or fluorine. The method adopts the new catalyst nickelous bromide and has characteristics of high reaction conversion rate and selectivity and short reaction time, and is easy for the industrial production.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a preparation method of o-nitrobenzonitrile compounds. Background technique [0002] Benzoylisoxazole herbicides (benzoylisoxazole herbicides), such as isoxaflutole (isoxaflutole), Pyrasulfotole, etc., are a new class of broad-spectrum herbicides with a new mechanism of action. Enzyme inhibitors, by inhibiting the synthesis of p-hydroxyphenylpyruvate dioxygenase, lead to the accumulation of tyrosine, hinder the biosynthesis of plastoquinone and tocopherol, and then affect the biosynthesis of carotenoids. [0003] O-nitrobenzonitrile compounds are one of the key intermediates for preparing benzoylisoxazole herbicides, and 2-nitro-4-trifluoromethylbenzonitrile in o-nitrobenzonitrile compounds is the key intermediate for preparing isoylisoxazole herbicides. One of the key intermediates of clomazone and Pyrasulfotole, as described in patents US5474998A and US6635780B1. ...

Claims

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Application Information

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IPC IPC(8): C07C253/14C07C255/50C07C323/62C07C319/20B01J27/128
Inventor 王文军宋蕾彭阳张政方勇刘世禄曹锦母灿先
Owner NUTRICHEM LAB CO LTD
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