Method for preparing 2-nitro-4-trifluoromethylbenzonitrile

A technology of trifluoromethyl benzonitrile and trifluoromethyl halobenzene, which is applied in the field of preparation of benzonitrile compounds, can solve the problems of long reaction time, low yield, expensive nickel bromide, etc., and meet the reaction conditions Gentle, easy-to-process effect

Active Publication Date: 2017-02-22
SHANDONG RUNBO BIOTECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, nickel bromide is expensive and should not be used in large quantities.
[0005] CN102675151A, using cuprous chloride and / or cuprous bromide as a catalyst, adopting 3-nitro-4-chlorobenzotrifluoride and potassium ferrocyanide to react to prepare products, but the reaction time is long and the yield is low,

Method used

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  • Method for preparing 2-nitro-4-trifluoromethylbenzonitrile

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Under the protection of dry nitrogen, add 90.2g of N-methylpyrrolidone and 13.4g of cuprous cyanide to the reaction bottle, heat up and reflux to separate water, cool down to 110°C, add 22.5g of 2-nitro-4-chlorotrifluorotoluene , catalyst 1.1g (dimethylaminopyridine 0.7g, potassium iodide 0.4g). Start stirring, heat to 150-160°C, and stir for 12 hours. Subsequently, the temperature was lowered to room temperature under the protection of nitrogen, and a sample was taken for GC analysis, and the reaction of the raw materials was completed. Add 60.0 g of ethyl acetate and 20.0 g of water, stir, separate the organic phase, extract the water phase with 20.0 g of ethyl acetate, combine the organic phases, dry over anhydrous sodium sulfate, and vacuum rectify to obtain 19.8 g of the product, with a yield of 91.5 %, LC content 98.1%. 2-nitro-4-trifluoromethylbenzonitrile mass spectrum data (EI) shows: 216 (M + ), 170 (M-NO 2 ).

Embodiment 2

[0025] Under the protection of dry nitrogen, add 88.7g of DMF and 11.2g of cuprous cyanide to the reaction flask, heat up and reflux to separate water, after the water is separated, cool down to 105°C, add 22.5 g, catalyst 1.3g (pyridine 0.8, potassium chloride 0.5g). Start stirring, heat to 150-160°C, and stir for 12 hours. Subsequently, the temperature was lowered to room temperature under the protection of nitrogen, and a sample was taken for GC analysis, and the reaction of the raw materials was completed. Add 60.0 g of ethyl acetate and 20.0 g of water, stir, separate the organic phase, extract the water phase with 20.0 g of ethyl acetate, combine the organic phases, dry over anhydrous sodium sulfate, and vacuum rectify to obtain 19.1 g of the product, with a yield of 88.4 %, LC content 97.2%.

Embodiment 3

[0027] Under the protection of dry nitrogen, add 95.6g of sulfolane and 14.6g of cuprous cyanide to the reaction flask, heat up and reflux to separate water, after water separation, cool down to 110°C, add 22.5g of 3-nitro-4-chlorotrifluorotoluene g, catalyst 0.3g (diisopropylethylamine 0.2g, potassium bromide 0.1g). Start stirring, heat to 150-160°C, and stir for 12 hours. Subsequently, the temperature was lowered to room temperature under the protection of nitrogen, and a sample was taken for GC analysis, and the reaction of the raw materials was completed. Add 60.0 g of ethyl acetate and 20.0 g of water, stir, separate the organic phase, extract the water phase with 20.0 g of ethyl acetate, combine the organic phases, dry over anhydrous sodium sulfate, and vacuum rectify to obtain 18.4 g of the product, with a yield of 85.3 %, LC content 95.7%.

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Abstract

The invention discloses a method for preparing 2-nitro-4-trifluoromethylbenzonitrile. The method includes the steps that cuprous cyanide is dissolved in N-methyl-2-pyrrolidone, then a catalyst is added, a thermal reaction is conducted for 8-14 h at 150-160 DEG C after addition, and GC detection is conducted till reaction of 2-nitro-4-(trifluoromethyl)halogenobenzene is finished; the product is cooled to room temperature, the solution is poured into a 40-50% ethyl acetate aqueous solution with the molar weight being 4.0-8.0 times that of a 2-nitro-4-trifluoromethylbenzonitrile crude product under the stirring condition, copper salt is filtered out, a filter cake is washed and extracted by means of ethyl acetate with the molar weight being 2-4 times that of 2-nitro-4-trifluoromethylbenzonitrile, oil layers are mixed and then washed with water, finally the product is dried with anhydrous magnesium sulfate and then subjected to vacuum rectification, and a 2-nitro-4-trifluoromethylbenzonitrile fine product is obtained. Use of virulent cyaniding reagents like sodium cyanide and potassium cyanide is avoided, the catalyst is used, reaction selectivity is improved, the yield is increased, the process is mild, and the yield reaches 90-93%.

Description

technical field [0001] The invention relates to a preparation method of benzonitrile compounds, in particular to a preparation method of 2-nitro-4-trifluoromethylbenzonitrile. Background technique [0002] 2-nitro-4-trifluoromethylbenzonitrile (NCB) is a special aromatic fluorine compound, which is an intermediate of many compounds such as medicine and pesticide. In terms of medicine, it is an intermediate for the synthesis of drugs for treating hypoglycemia, pain relief, and blood pressure lowering; in terms of pesticides, it is an intermediate of high-efficiency, low-toxicity, and low-consumption pesticides. NCB can also be used to prepare enol derivatives as herbicides, which are particularly effective for the control of drug-resistant weeds; the herbicides synthesized by introducing trifluoromethyl into the pyridine ring are hormone-type selective post-emergence herbicides, It is specially used to control broad-leaved weeds and is the main direction of development and r...

Claims

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Application Information

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IPC IPC(8): C07C253/14C07C255/50B01J31/26
CPCC07C253/14B01J27/08B01J27/10B01J31/0238B01J31/0244B01J31/26B01J2231/4205B01J35/19C07C255/50
Inventor 孙国庆侯永生绳敏陈桂元
Owner SHANDONG RUNBO BIOTECH CO LTD
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