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Synthetic method of fomesafen intermediate 2-chloro-4-trifluoromethylphenol

A technology of trifluoromethyl phenol and fomesafen, which is applied in chemical instruments and methods, preparation of organic compounds, production of bulk chemicals, etc., can solve the problem of high production cost of trifluoromethyl phenol, long reaction time, unsuitable Adopt and other problems to achieve the effect of convenient post-processing, short reaction time and improved yield

Inactive Publication Date: 2018-04-17
JIANGSU CHANGQING AGROCHEMICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

And because the raw material p-trifluoromethylphenol and p-trifluoromethylaniline used in the first two synthetic routes have higher production costs, so the first two synthetic routes should not be adopted
The raw material 3,4-dichloro-trifluorotoluene used in the third process route is easy to get, and the process is feasible, but the reaction time is longer and the yield is lower

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] A round bottom flask was charged with 4-(trifluoromethyl)benzaldehyde (1.54 g, 6.75 mmol, 1.0 equiv), and CH 2 Cl 2 (20 mL), then add mCPBA (1.52 g, 6.78 mmol, 1.0 equiv), stir at room temperature for 2 h, add 15 ml saturated NaHSO to the system after the reaction 3 The aqueous solution was transferred to a separatory funnel for extraction, the organic phases were collected and combined, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure to obtain 4-(trifluoromethyl)phenol with a yield of 71%. Add NCS (25.0 mmol, 3.4 g) and CH in a round bottom flask 2 Cl 2 (20.0 mL), cooled to -78 °C, added ZrCl 4 (0.5 mmol, 300 mg), followed by the addition of 4-(trifluoromethyl)phenol (25.0 mmol), the reaction was stirred at room temperature for 6 hours, after the reaction was completed, saturated NaHCO 3 The aqueous solution was extracted, the organic phases were collected and combined, and the solvent was removed to obtain 2-chloro-4-trifluo...

Embodiment 2

[0030] A round bottom flask was charged with 4-(trifluoromethyl)benzaldehyde (1.54 g, 6.75 mmol, 1.0 equiv), and CH 2 Cl 2 (20 mL), then add mCPBA (152 mg, 0.68 mmol, 0.1 equiv), stir at room temperature for 2 h, add 15 ml saturated NaHSO to the system after the reaction 3 The aqueous solution was transferred to a separatory funnel for extraction, the organic phases were collected and combined, dried with anhydrous sodium sulfate, and the solvent was removed under reduced pressure to obtain 4-(trifluoromethyl)phenol with a yield of 37%. Add NCS (25.0 mmol, 3.4 g) and CH in a round bottom flask 2 Cl 2 (20.0 mL), cooled to -78 °C, added ZrCl 4 (0.5 mmol, 300 mg), followed by the addition of 4-(trifluoromethyl)phenol (25.0 mmol), the reaction was stirred at room temperature for 6 hours, after the reaction was completed, saturated NaHCO 3 The aqueous solution was extracted, the organic phases were collected and combined, and the solvent was removed to obtain 2-chloro-4-trifluo...

Embodiment 3

[0032] A round bottom flask was charged with 4-(trifluoromethyl)benzaldehyde (1.54 g, 6.75 mmol, 1.0 equiv), and CH 2 Cl 2 (20 mL), then add mCPBA (1.52 g, 6.78 mmol, 1.0 equiv), stir at room temperature for 2 h, add 15 ml saturated NaHSO 3 The aqueous solution was transferred to a separatory funnel for extraction, the organic phases were collected and combined, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure to obtain 4-(trifluoromethyl)phenol with a yield of 71%. Add NCS (12.5 mmol, 1.7 g) and CH in a round bottom flask 2 Cl 2 (20.0 mL), cooled to -78 °C, added ZrCl 4 (0.5 mmol, 300 mg), followed by the addition of 4-(trifluoromethyl)phenol (25.0 mmol), the reaction was stirred at room temperature for 6 hours, after the reaction was completed, saturated NaHCO 3 The aqueous solution was extracted, the organic phases were collected and combined, and the solvent was removed to obtain 2-chloro-4-trifluoromethylphenol with a yield of 62...

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Abstract

The invention relates to a synthetic method of fomesafen intermediate 2-chloro-4-trifluoromethylphenol. 4-(Trifluoromethyl)benzaldehyde is used as a reaction material; mCPBA (meta-chloroperoxybenzoicacid) is used as an oxidant to convert 4-(trifluoromethyl)benzaldehyde into 4-(trifluoromethyl)phenol; NCS (N-chlorosuccinimide) is used to subject 4-(trifluoromethyl)benzaldehyde to chlorination to obtain the intermediate 2-chloro-4-trifluoromethylphenol. The method has the advantages that, for instance, the materials are easy to obtain, few byproducts are produced, little pollution is caused, reaction time is short and the yield is high.

Description

technical field [0001] The invention relates to a method for synthesizing 2-chloro-4-trifluoromethylphenol, an intermediate of fomesafen, and belongs to the technical field of synthesis of pesticide intermediates. Background technique [0002] Acifluorfen, fomesafen, lactofen, and acifluorfen are diphenyl ether herbicides, which are mainly used for post-emergence control of broad-leaved weeds, with high activity, broad herbicidal spectrum, With low toxicity, it is applied to cereal crops and has been widely used in northern my country. 2-Chloro-4-trifluoromethylphenol is an important intermediate in the synthesis of diphenyl ether herbicides, and it is also widely used in the synthesis of pesticides and medicines. So far, people have developed various methods for synthesizing 2-chloro-4-trifluoromethylphenol compounds, but all of these methods have the disadvantages of high raw material cost and low yield. [0003] There are three main traditional synthetic methods of 2-c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C37/01C07C39/24C07C37/62C07C39/26
CPCC07C37/01C07C37/62C07C39/24C07C39/26Y02P20/52
Inventor 于国权孙霞林马长庆丁华平
Owner JIANGSU CHANGQING AGROCHEMICAL CO LTD
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