Synthetic method of 4-iodoanisole

A technology of iodoanisole and synthesis method, which is applied in the field of synthesis of 4-iodoanisole, can solve problems such as instability of iodine chloride and complex synthesis route, and achieve safe and controllable reaction, simple and convenient post-treatment, and green reaction Effect

Active Publication Date: 2018-08-07
SINOPHARM CHEM REAGENT
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The object of the present invention is to provide a kind of synthetic method of 4-iodoanisole, to solve the problems such as complex synthetic route, unstable reactant iodine chloride in the prior art

Method used

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  • Synthetic method of 4-iodoanisole

Examples

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Comparison scheme
Effect test

Embodiment 1

[0022] A kind of synthetic method of 4-iodoanisole, comprises the following steps:

[0023] (1) prepare 2 moles of 20% NaI aqueous solution A and 2.1 moles of 8-10% sodium hypochlorite aqueous solution B for subsequent use;

[0024] (2) Add 900g of anisole into a 2L four-necked round-bottomed flask equipped with stirring, temperature display, and two constant pressure dropping funnels, and heat to 60-70°C under stirring; Add sodium iodide solution and sodium hypochlorite solution dropwise at the same time in a ratio of 1:1.05;

[0025] (3) After the dropwise addition, raise the temperature to 75-80°C and stir for 1 hour to obtain a light yellow reaction solution; cool to room temperature, stand to separate the phases; wash the organic phase with water, dry and filter to obtain the benzidine of 4-iodoanisole Ether solution, rectification, cooling, and solidification to obtain white massive crystals, namely 4-iodoanisole, the content of which is ≥98.5%, and the yield is 93.4%. ...

Embodiment 2

[0027] A kind of synthetic method of 4-iodoanisole, comprises the following steps:

[0028] (1) prepare 2 moles of 20% NaI aqueous solution A and 2 moles of 8-10% sodium hypochlorite aqueous solution B for subsequent use;

[0029] (2) Add 800g of anisole into a 2L four-necked round-bottomed flask equipped with stirring, temperature display, and two constant pressure dropping funnels, and heat to 60-70°C under stirring; Add sodium iodide solution and sodium hypochlorite solution dropwise at the same time in a ratio of 1:1;

[0030] (3) After the dropwise addition, raise the temperature to 75-80°C and stir for 1 hour to obtain a light yellow reaction solution; cool to room temperature, stand to separate the phases; wash the organic phase with water, dry and filter to obtain the benzidine of 4-iodoanisole The ether solution was rectified, cooled and solidified to obtain white blocky crystals, namely 4-iodoanisole, the content of which was ≥97%, and the yield was 91.2%.

Embodiment 3

[0032] A kind of synthetic method of 4-iodoanisole, comprises the following steps:

[0033] (1) prepare 2 moles of 20% NaI aqueous solution A and 2.2 moles of 8-10% sodium hypochlorite aqueous solution B for subsequent use;

[0034] (2) Add 770g of anisole into a 2L four-necked round-bottomed flask equipped with stirring, temperature display, and two constant pressure dropping funnels, and heat to 60-70°C under stirring; Add sodium iodide solution and sodium hypochlorite solution dropwise at the same time in a ratio of 1:1.1;

[0035] (3) After the dropwise addition, raise the temperature to 75-80°C and stir for 1 hour to obtain a light yellow reaction solution; cool to room temperature, stand to separate the phases; wash the organic phase with water, dry and filter to obtain the benzidine of 4-iodoanisole Ether solution, rectification, cooling, and solidification to obtain white massive crystals, that is, 4-iodoanisole, the content of which is ≥97%, and the yield is 90.6%. ...

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Abstract

The invention relates to the technical field of synthesis of drug intermediates and particularly relates to a synthetic method of 4-iodoanisole. The synthetic method comprises the following steps: with phenyl ether as a substrate, simultaneously dropwise adding a sodium hypochlorite solution and a sodium iodide solution in proportion so as to generate high-activity and fresh iodine chloride by virtue of sodium hypochlorite and sodium iodide, and dissolving iodine chloride into an anisole layer for iodization so as to generate a product; introducing byproduct hydrogen chloride into a water layer to be neutralized by iodine chloride byproduct sodium hydroxide; after the reaction is finished, naturally splitting phases, wherein organic phases are 4-iodoanisole and anisole; and carrying out post-treatment, so as to obtain 4-iodoanisole. The method is a reaction extraction process, a high-activity iodization agent, namely iodine chloride is immediately generated and is consumed for iodization, and an iodine chloride byproduct and an iodization byproduct immediately react to generate sodium chloride; and the reaction is environmentally friendly, efficient, safe and controllable.

Description

technical field [0001] The invention relates to the technical field of synthesis of pharmaceutical intermediates, in particular to a method for synthesizing 4-iodoanisole. Background technique [0002] 4-Iodoanisole is a white needle-like crystal with a melting point of 51-52°C and a boiling point of 237°C (96.8kPa). It is soluble in organic solvents such as alcohol and ether, but insoluble in water. 4-iodoanisole is an important general-purpose chemical reagent and a key synthetic intermediate in pharmaceuticals, liquid crystals, scientific research, etc., and is widely used in the field of organic synthesis. [0003] Usually 4-iodoanisole is synthesized by the reflux reaction of anisole and iodine chloride in acetic acid. Iodine chloride is a poisonous, corrosive, volatile solid, sensitive to air, light and moisture, and releases HCl gas when it meets water; it is unstable, and it is difficult to obtain a source with stable quality. Contents of the invention [0004] T...

Claims

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Application Information

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IPC IPC(8): C07C41/22C07C43/225C01B7/24
CPCC01B7/24C07C41/22C07C43/225
Inventor 郭建国秦建国孙蔚晨黄浩宋忠哲
Owner SINOPHARM CHEM REAGENT
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