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Method for synthesizing 2, 6-dibromo-4-cyanophenol

A synthesis method, cyanophenol technology, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve problems such as poor environmental protection, low yield, complicated operation, etc., and achieve low cost and high yield purity , the effect of simple steps

Active Publication Date: 2016-08-17
QUZHOU YINGTE HIGH MOLECULAR MATERIAL CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The object of the present invention is to provide a kind of synthetic method of 2,6-dibromo-4-cyanophenol, which solves the problems of low yield, complex operation and The problem of poor environmental protection

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Add 4 g (0.034 mol) of p-cyanophenol, 9.18 g (0.034 mol) of potassium persulfate and 7.6 g (0.074 mol) of sodium bromide into a 100 mL round bottom flask, add 60 mL of 50% ethanol aqueous solution, stir, and React at 50°C for 4 hours. After the reaction, filter, wash the filter cake with water, and dry to obtain the product 2,6-dibromo-4-cyanophenol, which is a white solid with a yield of 92% and a purity of 98% by HPLC. The nuclear magnetic resonance test was carried out with a Swiss Bruker AV-400 NMR spectrometer. The measurement conditions were: the separated and purified product was dissolved in deuterated chloroform for testing. The analysis results were: 1 H NMR (400 MHz, CDCl 3 ) δ 7.78 (s, 2H), 6.38 (s, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ 153.59, 135.65, 116.21, 110.41, 106.55.

Embodiment 2

[0023] Add 4 g (0.034 mol) p-cyanophenol, 9 g (0.037 mol) sodium persulfate and 10.1 g (0.085 mol) potassium bromide to a 100 mL round bottom flask, add 40 mL of 50% methanol aqueous solution, stir, and The reaction was irradiated under ultraviolet light for 8 hours. After the reaction, filter, wash the filter cake with water, and dry to obtain the product 2,6-dibromo-4-cyanophenol, which is a white solid with a yield of 94% and a purity of 98% by HPLC. .

Embodiment 3

[0025] Add 4 g (0.034 mol) p-cyanophenol, 31 g (0.136 mol) ammonium persulfate and 39 g (0.272 mol) cuprous bromide to a 100 mL round bottom flask, add N,N-dimethylformamide 80 mL, stirred, and reacted at 30°C for 10 hours. After the reaction, filtered, washed the filter cake with water, and dried to obtain the product 2,6-dibromo-4-cyanophenol, which was a white solid with a yield of 95.2%. HPLC The purity is 97.6%.

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PUM

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Abstract

The invention provides a method for synthesizing 2, 6-dibromo-4-cyanophenol. The method includes a particular operation step of carrying out reaction on 4-cyanol phenol and bromine such as sodium bromine and potassium bromine in air or nitrogen atmosphere in the presence of persulfate and solvents under heating or illumination conditions. The method has the advantages that the method is safe and reliable, is high in yield, free of pollution and easy to implement, is an environment-friendly chemical process and can be used for preparing the 2, 6-dibromo-4-cyanophenol, and reaction conditions are mild.

Description

technical field [0001] The invention relates to the technical field of chemical industry, in particular to a synthesis method of 2,6-dibromo-4-cyanophenol. Background technique [0002] 2,6-dibromo-4-cyanophenol, also known as bromoxynil, this compound and its octanoate, sodium salt, potassium salt and other forms are widely used as contact insecticides for selective post-emergence stem and leaf treatment . It is mainly absorbed by the leaves, and rapidly causes tissue necrosis by inhibiting the various processes of photosynthesis. It is suitable for crop fields such as wheat, barley, rye, corn, sorghum, flax, etc. to control broad-leaved weeds Polygonum, quinoa, amaranth, bottle grass, black nightshade, cocklebur, wheat father-in-law , pig hair dish, field bindweed, buckwheat vine and other annual dicotyledonous weeds. Bromoxynil is stable in storage and generally does not react with other herbicides. In addition to being used alone, it can also be mixed with a variety o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/53C07C253/30
CPCC07C253/30C07C255/53
Inventor 夏吾炯刘强郭小忠冯永胜徐景祥章丽袁鹏
Owner QUZHOU YINGTE HIGH MOLECULAR MATERIAL CO LTD
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