Novel synthesis method of aromatic 5-chloro-2-fluoro-4-(trifluoromethyl) aniline hydrochloride containing trifluoromethyl intermediate

A technology of aniline hydrochloride and synthesis method, applied in new synthesis field, can solve problems such as low yield, and achieve the effects of high yield, wide applicability and high purity

Inactive Publication Date: 2017-11-24
梁江丽
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

So far, only one patent (EP246061A2, 1987) in the Reaxys database has reported the synthesis of t...

Method used

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  • Novel synthesis method of aromatic 5-chloro-2-fluoro-4-(trifluoromethyl) aniline hydrochloride containing trifluoromethyl intermediate
  • Novel synthesis method of aromatic 5-chloro-2-fluoro-4-(trifluoromethyl) aniline hydrochloride containing trifluoromethyl intermediate
  • Novel synthesis method of aromatic 5-chloro-2-fluoro-4-(trifluoromethyl) aniline hydrochloride containing trifluoromethyl intermediate

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Experimental program
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Effect test

Embodiment 1

[0019] In a 2 L three-necked flask, dissolve 68.58 g (270 mmol) iodine element and 83.7 g (270 mmol) silver sulfate in 1.5 L absolute ethanol solution, and stir and cool the reaction solution to 0-5°C. 39.15 g (270 mmol) of 5-chloro-2-fluoroaniline was quickly added to the reaction solution. During the addition, the reaction temperature was kept at 0-5°C, and then slowly raised to room temperature for 1 hr. TLC (petroleum ether / ethyl acetate=1 / 8) traced the disappearance of the starting material, quenched with water (250 mL), and extracted with ethyl acetate (3×250 mL). The organic phase was washed with saturated sodium thiosulfate solution (35.6%) (3×300 mL), and dried over anhydrous sodium sulfate. The solvent was removed, and the crude product (about 80 g) was purified by column chromatography (gradient elution procedure: petroleum ether, petroleum ether / ethyl acetate=3 / 10), and the eluent was placed at room temperature, evaporated and concentrated to obtain a white Solid ...

Embodiment 2

[0021] In a 2 L three-necked flask, 54.2 g (200 mmol) of compound A and 55.3 mL (400 mmol) of triethylamine were dissolved in 1.5 L of dry dichloromethane solution, and the reaction solution was stirred and cooled to 0-5 °C. Add 17.1 mL (240 mmol) of acetyl chloride to the reaction solution slowly dropwise. During the addition, the reaction temperature is kept at 0-5°C, then slowly rise to room temperature, and react for 1 hr. TLC (petroleum ether / ethyl acetate=1 / 10) traced the disappearance of the starting material, quenched with water (250 mL), and extracted with dichloromethane (3×200 mL). The organic phase was washed with saturated sodium chloride solution (3×200 mL), dried over anhydrous sodium sulfate, and concentrated by evaporation to obtain 60.0 g of compound B as a white solid (yield 96%).

[0022] In a 1 L three-necked flask, 31.3 g (100 mmol) of compound B, 89.5 g (500 mmol) of hexamethylphosphoric triamide and 29.2 g (150 mmol) of copper iodide were dissolved in 0...

Embodiment 3

[0024] In a 500 mL three-neck flask, 12.75 g (50 mmol) of compound C was dissolved in 200 mL absolute ethanol solution, 100 mL (600 mmol) of 6 mol / L hydrochloric acid was added at room temperature, and the reaction solution was heated to reflux for 3 hr. Then slowly warm to room temperature. TLC (petroleum ether / ethyl acetate=1 / 7) traced the disappearance of the raw material, and the reaction solution was evaporated and concentrated at low temperature to obtain 11.2 g of compound D as a brown solid (yield 90%). 1 H NMR (400 MHz, DMSO-d6) δ: 6.92 ~7.06 (4 H, m), 7.42 ~7.50 (1 H, m).

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Abstract

The invention discloses a novel synthesis method of aromatic 5-chloro-2-fluoro-4-(trifluoromethyl) aniline hydrochloride containing a trifluoromethyl intermediate. The method comprises steps as follows: 1) 5-chloro-2-fluoroaniline, elemental iodine and the like are subjected to an iodination reaction in an anhydrous ethanol solution; 2) with dichloromethane as a solvent, an obtained aromatic iodination product is subjected to an acetylation reaction; 3) the aromatic iodination product protected by acetyl, methyl fluorosulphonyldifluoroacetate and the like are subjected to a trifluoromethylation reaction at the temperature of 80 DEG C; 4) finally, 6 mol/L hydrochloric acid is used for a deacetylation reaction in ethanol, and a target product is obtained. The novel synthesis method has the advantages that the route design is novel, the product purity is good and operation is safe, simple and convenient; all reactions are stably conducted in the solvent, the process is easy to control, few crude product impurities exist, purification is easy, and the quality and yield of the product are increased. The total yield of the route is 66%, the product purity can reach 98.5%, and the novel synthesis method has higher research and development application value.

Description

technical field [0001] The invention relates to a new synthesis method, in particular to an intermediate compound for synthesizing 5-chloro-2-fluoro-4-(trifluoromethyl)aniline hydrochloride and a synthesis method thereof. Background technique [0002] Fluorine-containing compounds have the characteristics of high membrane permeability, anti-metabolic stability, affinity with lipid membranes, thermal stability and chemical stability, and have been widely used in pesticides. The advantages of fluorine-containing pesticides, such as high selectivity, high applicability, high added value, low cost, low toxicity, low residue, and environmental friendliness, are in line with the development trend of contemporary pesticides. In the past ten years, among the newly developed chemical pesticides in the world, fluorine-containing pesticides accounted for about 40%, but among the more than 200 types of pesticides produced in my country, fluorine-containing pesticides produced on a large...

Claims

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Application Information

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IPC IPC(8): C07C209/74C07C211/52C07C231/02C07C233/15C07C231/12C07C209/00
CPCC07C209/74C07C209/00C07C211/52C07C231/02C07C231/12C07C233/15
Inventor 梁亭梁江丽李军罗强刘宇
Owner 梁江丽
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