Preparation method of 2, 4, 6-trichlorobenzonitrile

A technology of trichlorobenzonitrile and trichlorobenzene, which is applied in the field of preparation of 2,4,6-trichlorobenzonitrile, can solve the problems of high cost, environmental pollution, and large amount of three wastes, and achieve low cost and simple and easy reagents The effect of gaining and short route

Pending Publication Date: 2021-06-25
上海立科化学科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] Literature (Chemische Berichte, 1894, vol.27, p.3151) discloses that 2,4,6-trichloroaniline is used as raw material to prepare 2,4,6-trichlorobenzonitrile by Sandmeymer reaction, and the preparation process is shown as Reaction equation C, this process introduces cyano group through diazotization reaction, which has defects such as high cost, large amount of three wastes, and serious environmental pollution

Method used

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  • Preparation method of 2, 4, 6-trichlorobenzonitrile
  • Preparation method of 2, 4, 6-trichlorobenzonitrile

Examples

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Embodiment 1

[0031] (1) Synthesis of 2-bromo-1,3,5-trichlorobenzene

[0032] Dissolve s-trichlorobenzene (100 g, 1.00 eq.) in dry dichloromethane (1200 ml), add ferric chloride, raise the temperature to 20-30°C, add liquid bromine (96.8 g, 1.1 eq.), dropwise After the addition, continue to maintain 20-30 ° C, react for 5 hours (HPLC detection reaction raw materials ≤ 2.0%), cool down to room temperature, pour the reaction system into 15% sodium bisulfite solution (600 g) to quench the reaction , after standing for stratification, separate the organic phase, then wash the organic phase with 15% aqueous sodium bisulfite solution (300 g) and saturated brine (500 g) successively, then stand for stratification, and separate the organic phase again , the separated organic phase was dried and concentrated to obtain 2-bromo-1,3,5-trichlorobenzene product (light yellow solid, about 140.4 g), with a yield of 97.79% and a purity of 94.50%.

[0033] (2) Synthesis of 2,4,6-trichlorobenzonitrile

[00...

Embodiment 2

[0038] (1) Synthesis of 2-bromo-1,3,5-trichlorobenzene

[0039] Dissolve s-trichlorobenzene (150 g, 1.0 eq) in dry dichloromethane (1200 ml), add ferric chloride, raise the temperature to 20-30°C, add liquid bromine (158.2 g, 1.2 eq), dropwise After the addition, continue to maintain 20-30 ° C, react for 5 hours (HPLC detection reaction raw materials ≤ 2.0%), cool down to room temperature, pour the reaction system into 15% sodium bisulfite solution (900 g) to quench the reaction , after standing for stratification, separate the organic phase, then wash the organic phase with 15% aqueous sodium bisulfite solution (450 g) and saturated brine (750 g) successively, then stand for stratification, and separate the organic phase again , the separated organic phase was dried and concentrated to obtain 2-bromo-1,3,5-trichlorobenzene product (pale yellow solid, about 211.4 g), with a yield of 98.20% and a purity of 96.20%.

[0040] (2) Synthesis of 2,4,6-trichlorobenzonitrile

[0041]...

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Abstract

The invention provides a preparation method of 2, 4, 6-trichlorobenzonitrile. The method comprises the following steps: (1) contacting 1, 3, 5-trichlorobenzene with a bromination reagent in an aprotic solvent to carry out bromination reaction to prepare 2-bromo-1, 3, 5-trichlorobenzene; and (2) enabling the 2-bromo-1, 3, 5-trichlorobenzene to make contact with a cyaniding reagent in a dipolar aprotic solvent to carry out cyaniding reaction so as to prepare the 2, 4, 6-trichlorobenzonitrile. The 1, 3, 5-trichlorobenzene which is low in price and easy to obtain is used as the raw material, the bromination reaction and the cyanidation reaction are sequentially carried out in the specific solvent, the raw material conversion rate is high, and the 2, 4, 6-trichlorobenzonitrile has the advantages of high yield and purity, short route, simple process, low cost, environmental protection and the like.

Description

technical field [0001] The invention relates to a preparation method of 2,4,6-trichlorobenzonitrile, which belongs to the field of chemical synthesis. Background technique [0002] Fluorine is the most electronegative element. The introduction of fluorine atoms makes fluorine-containing organic compounds have unique physical properties, chemical properties and physiological activities, and exhibits good chemical stability, surface activity, temperature resistance and corrosion resistance. The fluorine-containing materials are widely used in biochemistry, pesticides, functional materials and other fields. 2,4,6-Trichlorobenzonitrile compounds are the raw materials of many fluorine-containing compounds, such as intermediates of medicines, pesticides, and liquid crystal materials, and have important application value and market prospects. [0003] At present, the synthesis process of 2,4,6-trichlorobenzonitrile compounds generally has problems such as complex process, high cos...

Claims

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Application Information

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IPC IPC(8): C07C253/14C07C255/50
CPCC07C253/14C07C255/50
Inventor 曾海峰
Owner 上海立科化学科技有限公司
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