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Mass production method for 4-chloro-2'-cyanobiphenyl

A technology of cyanobiphenyl and chlorobromobenzene, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of many pollutants, many by-products, unfavorable large-scale industrial production, etc., and achieve post-processing Simple, less polluting effect

Inactive Publication Date: 2016-11-16
JIANGSU FLAG CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] However, expensive 4-chlorophenylboronic acid is used in the above-mentioned prior art, and the preparation conditions are harsh, which limits industrialization. At the same time, the selectivity is poor, there are many by-products, and there are many pollutants, which is not conducive to large-scale industrial production.

Method used

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  • Mass production method for 4-chloro-2'-cyanobiphenyl
  • Mass production method for 4-chloro-2'-cyanobiphenyl

Examples

Experimental program
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Effect test

Embodiment 1

[0024] Embodiment 1: the preparation of Grignard reagent p-tolylmagnesium chloride

[0025] Under nitrogen protection, in a 2000 ml four-neck flask equipped with a reflux condenser, a constant pressure dropping funnel and a stirring device, add 24.3 grams of magnesium powder (1.0 moles), 19.15 grams of 4-chlorobromobenzene (0.10 moles) and 100 Milliliter of tetrahydrofuran, start stirring, heat up to 75°C, add appropriate amount of crystalline iodine to initiate the reaction. A mixed solution of 172.4 g of 4-chlorobromobenzene (0.9 mol) and 900 ml of tetrahydrofuran was added dropwise at the same temperature, and the dropwise addition was completed in 1 hour. Cool to room temperature and set aside.

Embodiment 2

[0026] Embodiment 2: Preparation of 4-chloro-2'-cyanobiphenyl

[0027] Under the protection of nitrogen, in a 2000 ml four-neck flask equipped with a reflux condenser, a constant pressure dropping funnel and a stirring device, add 25.18 g of anhydrous manganese chloride (0.2 mol) and 137.6 g of 2-chlorobenzene Nitrile (1.0 mol) and 200 ml of tetrahydrofuran, stirred, cooled to -5°C in an ice-salt bath, added dropwise the Grignard reaction solution of Example 1, after 1 hour of dripping, the reaction solution was kept at -5-0°C for 2 hours . Recover tetrahydrofuran from the reaction solution under normal pressure, add 500 ml of toluene to the residue, adjust the pH to 2 with 6mol / L hydrochloric acid, separate the layers, wash the organic phase with saturated brine (250 mL*4), dry over anhydrous sodium sulfate, and filter , Toluene was recovered from the filtrate under normal pressure, and the 170-175°C / 0.1MPa fraction was collected by vacuum distillation to obtain 181.6 grams ...

Embodiment 3

[0028] Embodiment 3: Preparation of 4-chloro-2'-cyanobiphenyl

[0029] Under the protection of nitrogen, in a 2000 ml four-necked bottle equipped with a reflux condenser, a constant pressure dropping funnel and a stirring device, add 62.95 g of anhydrous manganese chloride (0.5 mol) and 137.6 g of 2-chlorobenzene Nitrile (1.0 mol) and 200 ml of tetrahydrofuran, stirred, cooled to -5°C in an ice-salt bath, added dropwise the Grignard reaction solution of Example 1, after 1 hour of dripping, the reaction solution was kept at -5-0°C for 2 hours . Recover tetrahydrofuran from the reaction solution under normal pressure, add 500 ml of toluene to the residue, adjust the pH to 2 with 6mol / L hydrochloric acid, separate the layers, wash the organic phase with saturated brine (250 mL*4), dry over anhydrous sodium sulfate, and filter , toluene was recovered from the filtrate under normal pressure, and the 170-175°C / 0.1MPa fraction was collected by vacuum distillation to obtain 183.7 gra...

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Abstract

The invention discloses a mass production method for 4-chloro-2'-cyanobiphenyl. The mass production method comprises the following steps: para chlorobromobenzene and magnesium chips in a mole ratio being (1:1)-(1:5) are added to anhydrous tetrahydrofuran for a reaction under protection of nitrogen, and a Grignard reagent is prepared; 2-chlorobenzonitrile, a manganese compound catalyst and anhydrous tetrahydrofuran are mixed, then the Grignard reagent is added slowly to the mixture for a reaction, tetrahydrofuran is recovered after the reaction through filtration and desolvation, toluene is added, the pH value is regulated with an acid to be 1-5, an organic phase is separated out, the solvent is removed, and 4-chloro-2'-cyanobiphenyl is obtained. The raw materials are cheap and easily available, the total yield is higher, aftertreatment is simpler, and less pollution is caused.

Description

technical field [0001] The invention relates to the technical field of fine chemicals, in particular to a large-scale production process of a fine chemical intermediate, 4-chloro-2'-cyanobiphenyl. Background technique [0002] 4-Chloro-2'-cyanobiphenyl is an important intermediate of the pesticide fungicide boscalid. Boscalid is a new type of nicotinamide fungicide developed by BASF in Germany. It is mainly used to prevent and control powdery mildew, gray mold, various rots, brown rot and root rot. Registered in Germany and Switzerland. The English name of boscalid: Boscalid, chemical name: 2-chloro-N-(4'-chlorodiphenyl-2-yl) nicotinamide, chemical molecular formula: C18H12Cl2N2O, molecular weight: 343.21, toxicity: acute oral:> 2000mg / kg; acute transdermal: >2000mg / kg, which is a low-toxic fungicide. [0003] Boscalid belongs to the succinate coenzyme Q reductase inhibitor in the mitochondrial respiratory chain, which has a strong inhibitory ability to spore germin...

Claims

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Application Information

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IPC IPC(8): C07C253/30C07C255/50
CPCC07C253/30C07C255/50
Inventor 王凤云剧宗峰李宏举吴耀军
Owner JIANGSU FLAG CHEM IND
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