Preparation method for 2-nitro-4-(trifluoromethyl)benzonitrile

A technology of trifluoromethylbenzonitrile and chlorotrifluorotoluene is applied in the field of preparation of 2-nitro-4-trifluoromethylbenzonitrile and can solve the problem of 3-nitro-4-bromotrifluorotoluene Expensive, difficult to obtain, complex process and other problems, to achieve the effect of increasing selectivity and conversion rate, easy availability of raw materials, and simple process

Inactive Publication Date: 2015-12-23
青岛和兴精细化学有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] 2-nitro-4-trifluoromethylbenzonitrile is one of the key intermediates for the preparation of isoxaflutole herbicide, but the existing preparation method of 2-nitro-4-trifluoromethylbenzonitrile High cost and complex process
[0004] Patent US4886936 provides a method for using 3-nitro-4-bromobenzotrifluoride and cuprous cyanide as raw materials to synthesize 2-nitro-4-trifluoromethylbenzonitrile. The method does not use a catalyst, and the reaction Both selectivity and conversion can reach 95%, but 3-nitro-4-bromobenzotrifluoride is expensive and difficult to obtain

Method used

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  • Preparation method for 2-nitro-4-(trifluoromethyl)benzonitrile
  • Preparation method for 2-nitro-4-(trifluoromethyl)benzonitrile
  • Preparation method for 2-nitro-4-(trifluoromethyl)benzonitrile

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Under mechanical stirring and nitrogen protection, 258.0 g (1 mol) of 3-nitro-4-chlorobenzotrifluoride, 53.9 g (1.1 mol) of sodium cyanide, 143.0 g (1 mol) of cuprous bromide, 2.2g (0.01mol) of 1-butyl-3-methylimidazolium bromide, 99.0g (1mol) of N-methylpyrrolidone as a solvent, heat up under mechanical stirring, keep at 185°C for 3 hours, then raise the temperature to 192°C for 5 hours, The reaction is over. The conversion rate is 96.46% and the selectivity is 95.14% as detected by GC, and the content of the product obtained by rectification can reach more than 99% as detected by GC.

[0027] Such as figure 1 As shown in the GC detection chart, it can be seen from the figure that the retention time is 2.51min and the peak area is 3.54, indicating that the content of the raw material 3-nitro-4-chlorotrifluoromethyl toluene is 3.54%, so its conversion rate is 96.46%, and the retention time The peak area at 7.37min was 91.77, indicating that the content of the product ...

Embodiment 2

[0029] Under mechanical stirring and nitrogen protection, 258.0g (1mol) of 3-nitro-4-chlorobenzotrifluoride, 98.5g (1.1mol) of cuprous cyanide, 218.5g (1mol) of nickel bromide, 1.7g (0.01mol) of 1-butyl-3-methylimidazolium chloride salt, 99.0g (1mol) of N-methylpyrrolidone as a solvent, heat up under mechanical stirring, keep at 185°C for 3 hours, then raise the temperature to 193°C for 5 hours, The reaction is over. According to GC detection, the conversion rate is 96.73%, and the selectivity is 95.20%. The content of the product obtained through rectification can reach more than 99% through GC detection.

[0030] Such as figure 2 As shown in the GC detection chart, it can be seen from the figure that the retention time is 2.52min and the peak area is 3.27, indicating that the content of the raw material 3-nitro-4-chlorotrifluoromethyltoluene is 3.27%, so its conversion rate is 96.73%, and the retention The peak area at time 7.25min was 92.09, indicating that the content o...

Embodiment 3

[0032] Under mechanical stirring and nitrogen protection, 258.0g (1mol) of 3-nitro-4-chlorobenzotrifluoride, 98.5g (1.1mol) of cuprous cyanide, and 143.0g (1mol) of cuprous bromide were successively added to the reactor , 2.1g (0.01mol) of 1-propyl-3-methylimidazolium bromide, 99.0g (1mol) of N-methylpyrrolidone as a solvent, heat up under mechanical stirring, keep warm at 185°C for 4 hours, then heat up to 195°C for 5 hours , the reaction ends. The conversion rate is 96.95% and the selectivity is 95.65% through GC detection, and the content of the product obtained through rectification can reach more than 99% through GC detection.

[0033] Such as image 3 As shown in the GC detection chart, it can be seen from the figure that the retention time is 2.51min and the peak area is 4.05, indicating that the raw material 3-nitro-4-chlorotrifluoromethyltoluene content is 3.05%, so its conversion rate is 96.95%, and the retention Time 7.16min peak area is 92.73, illustrates that th...

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Abstract

The invention provides a preparation method for 2-nitro-4-(trifluoromethyl)benzonitrile. The method comprises the following steps: under the protection of nitrogen, successively adding 3-nitro-4-chlorobenzotrifluoride, cyanide, a catalyst II, a catalyst II and a solvent N-methyl-2-pyrrolidone into a reactor; carrying out heating under mechanical stirring; carrying out a reaction at temperature of 185 to 195 DEG C for 5 to 9 h; and then carrying out rectification so as to obtain 2-nitro-4-(trifluoromethyl)benzonitrile. The cyanide is one or more selected from the group consisting of sodium cyanide, potassium cyanide and cuprous cyanide; the catalyst I is one or two selected from the group consisting of cuprous bromide and nickel bromide; and the catalyst II is methylimidazole ionic liquid. According to the preparation method in the invention, the two catalysts are used and reaction temperature is adjusted in stages, so selectivity and conversion rate of the reaction are improved, cost is substantially reduced, and the preparation method is simple.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of 2-nitro-4-trifluoromethylbenzonitrile. Background technique [0002] Isoxaflutole herbicide belongs to p-hydroxyphenylpyruvate dioxygenase inhibitors, it metabolizes rapidly in plants and soil, opens the isoxazole ring to form diketonitrile, and exerts herbicidal effect. P-hydroxyphenylpyruvate dioxygenase converts p-hydroxyphenylpyruvate to homogentisate, a key step in plastoquinone biosynthesis. Inhibition of p-hydroxyphenylpyruvate dioxygenase by isoxaflutole indirectly inhibits carotenoid biosynthesis, thereby causing yellowing of nascent tissues. Isoxaflutole is widely used in corn and sugarcane fields to control gramineous weeds and broadleaf weeds. [0003] 2-nitro-4-trifluoromethylbenzonitrile is one of the key intermediates for the preparation of isoxaflutole herbicide, but the existing preparation method of 2-nitro-4-trifl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/50C07C253/14B01J31/26
Inventor 盖钧一翟淑萍佘蕾张文传周国芳孙晓伟石晓庆
Owner 青岛和兴精细化学有限公司
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