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Preparation process of 3,5-dichloro-2-iodoanisole

A technology for the preparation of iodoanisole and its preparation technology, which is applied in the field of preparation technology of 3,5-dichloro-2-iodoanisole, can solve problems such as careless operation, high price, and easy occurrence of danger, and meet the reaction conditions Gentle, Inexpensive Effects

Pending Publication Date: 2021-11-05
苏州求索生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The silver tetrafluoroborate used in this method is a dangerous product, which is prone to danger due to careless operation, and is expensive, which has certain limitations.

Method used

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  • Preparation process of 3,5-dichloro-2-iodoanisole
  • Preparation process of 3,5-dichloro-2-iodoanisole
  • Preparation process of 3,5-dichloro-2-iodoanisole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Add 3,5-dichlorophenol (20g, 122.7mmol) and methyl tert-butyl ether (200ml) into a three-necked flask, and stir evenly;

[0036] Lower the temperature of the system to -10°C, add sodium hydride (5 g, 208.3 mmol) in small amounts and mix well;

[0037] Restore the system temperature to room temperature, and stir for 30 minutes;

[0038] Lower the temperature of the system again to -10°C, slowly add iodine (31.2g, 122.9mmol), after the addition is complete, restore the system to room temperature, and stir the reaction overnight;

[0039] Dilute hydrochloric acid (100ml) was added to quench the reaction, and after stirring, ethyl acetate (200ml*3) was added for extraction;

[0040] The organic layers were combined, rinsed twice with saturated brine, dried once with anhydrous magnesium sulfate, and evaporated to dryness to obtain the intermediate product 3,5-dichloro-2-iodophenol;

[0041] Add the intermediate product 3,5-dichloro-2-iodophenol (5g, 17.3mmol), cesium carbo...

Embodiment 2

[0047] Add 3,5-dichlorophenol (20g, 122.7mmol) and methanol (300ml) into a three-necked flask, and stir evenly;

[0048] The temperature of the system was lowered to -20°C, sodium hydroxide (14.7g, 367.5mmol) was added in small amounts and stirred evenly.

[0049] Return the system temperature to room temperature, and stir the reaction for 2h;

[0050] The temperature of the system was then lowered to -20°C, and iodine (93.4 g, 368.0 mmol) was slowly added. After the addition was complete, the system was returned to room temperature, and the reaction was stirred overnight.

[0051] Add concentrated hydrochloric acid (100ml) to quench the reaction, add ethyl acetate (200ml*3) to extract after stirring;

[0052] The organic layers were combined, rinsed twice with saturated brine, dried once with anhydrous magnesium sulfate, and evaporated to dryness to obtain the intermediate product 3,5-dichloro-2-iodophenol.

[0053] Add the intermediate product 3,5-dichloro-2-iodophenol (5g...

Embodiment 3

[0059] Add 3,5-dichlorophenol (20g, 122.7mmol) and toluene (200ml) into a three-necked flask, and stir evenly;

[0060] Lower the temperature of the system to -40°C, add potassium hydroxide (34.4g, 613.2mmol) in small amounts, and stir evenly;

[0061] Return the system temperature to room temperature, and stir for 5 hours;

[0062] The temperature of the system was lowered to -40°C again, and iodine (31.1 g, 122.7 mmol) was slowly added. After the addition was complete, the system was returned to room temperature, and the reaction was stirred overnight.

[0063] Add glacial acetic acid (500ml) to quench the reaction, add ethyl acetate (200ml*3) to extract after stirring;

[0064] The organic layers were combined, rinsed twice with saturated brine, dried once with anhydrous magnesium sulfate, and evaporated to dryness to obtain the intermediate product 3,5-dichloro-2-iodophenol.

[0065] Add the intermediate product 3,5-dichloro-2-iodophenol (5g, 17.3mmol), potassium carbona...

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Abstract

The invention relates to a preparation process of 3,5-dichloro-2-iodoanisole. The preparation process comprises the following steps: sequentially adding 3,5-dichlorophenol and an organic solvent into a container, adding alkali at low temperature, carrying out uniform stirring, then recovering the temperature of a system to room temperature, performing stirring and reacting for quantitative time, slowly adding iodine at low temperature, gradually recovering to room temperature, conducting stirring overnight, quenching a reaction with acid, adding ethyl acetate for extraction, combining organic layers to obtain an intermediate product 3,5-dichloro-2-iodophenol, sequentially adding 3,5-dichloro-2-iodophenol, alkali and an organic solvent into the container, adding a methylation reagent, carrying out stirring for a reaction overnight under the condition of nitrogen protection, pouring reaction liquid into ice water, adding an organic solvent for extraction, and finally combining organic layers to obtain the final product 3, 5-dichloro-2-iodoanisole. The method is mild in reaction conditions, low in raw material price and free of dangerous goods, and has great advantages when being put into large-batch production.

Description

technical field [0001] The invention relates to the technical field of medicine synthesis, in particular to a preparation process of 3,5-dichloro-2-iodoanisole. Background technique [0002] 3,5-dichloro-2-iodoanisole is an important API intermediate, which often appears in the synthesis of many new drugs; in the existing synthetic technology, 3,5-dichloro-2-iodoanisole The ether is mainly obtained by reacting the raw material 3,5-dichloroanisole with silver tetrafluoroborate and iodine. The synthetic route is as follows: [0003] [0004] The silver tetrafluoroborate used in this method is a dangerous product, which is prone to danger due to careless operation, and is expensive, which has certain limitations. Contents of the invention [0005] The purpose of the present invention is to provide a preparation process of 3,5-dichloro-2-iodoanisole in order to overcome the deficiencies of the prior art. [0006] In order to achieve the above object, the technical solutio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C43/225C07C41/16C07C41/38C07C41/34
CPCC07C41/16C07C41/38C07C41/34C07C37/62C07C43/225C07C39/30
Inventor 汤健志刘相国蔡蓉蓉
Owner 苏州求索生物科技有限公司