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Preparation method of 2-bromo-3-methoxypyridine

A technology of methoxypyridine and hydroxypyridine, which is applied in the field of preparation of 2-bromo-3-methoxypyridine, can solve the problems of long synthesis route, troublesome post-processing, low yield and the like, and achieves short route and reaction conditions. Gentle, high-yield effect

Inactive Publication Date: 2020-01-21
常州传侑环保科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The existing method for preparing 2-bromo-3-methoxypyridine has a long synthetic route, harsh process conditions, low yield, and troublesome post-processing

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] (1) Preparation of 2-bromo-3-hydroxypyridine: Cool 60ml of 40% aqueous sodium hydroxide solution to -10-0°C with an ice-salt bath, and add 16g (0.1mol) of liquid bromine dropwise within this temperature range; Dissolve 9.8g (0.1mol) of 3-hydroxypyridine in 50ml of 40% aqueous sodium hydroxide solution, and then add this solution dropwise to the above liquid bromine solution, keeping the system temperature at 10°C; after the dropwise addition, stir at room temperature for 2.5 hours , and then adjust the pH to 7 with acid; the resulting crude product was recrystallized to obtain 2-bromo-3-hydroxypyridine with a yield of 70%.

[0016] (2) Preparation of 2-bromo-3-methoxypyridine: add 0.7g of sodium to 20ml of methanol, heat the oil bath to reflux, keep the system reflux, dissolve 5g of 2-bromo-3-hydroxypyridine in 50ml of DMF , then added dropwise to the methanol solution of sodium; stirred for 10 minutes, removed most of the methanol by distillation under reduced pressure...

Embodiment 2

[0018] (1) Preparation of 2-bromo-3-hydroxypyridine: Cool 60ml of 40% aqueous sodium hydroxide solution to -10-0°C with an ice-salt bath, and add 16g (0.1mol) of liquid bromine dropwise within this temperature range; Dissolve 9.8g (0.1mol) of 3-hydroxypyridine in 50ml of 40% aqueous sodium hydroxide solution, and then add this solution dropwise to the above liquid bromine solution, keeping the system temperature at 15°C; after the dropwise addition, stir at room temperature for 3 hours , and then adjust the pH to 7 with acid; the resulting crude product was recrystallized to obtain 2-bromo-3-hydroxypyridine with a yield of 75%.

[0019] (2) Preparation of 2-bromo-3-methoxypyridine: Add 0.7g of sodium to 30ml of methanol, heat the oil bath to reflux, keep the system reflux, dissolve 5g of 2-bromo-3-hydroxypyridine in 50ml of DMF , then added dropwise to the methanol solution of sodium; stirred for 15 minutes, removed most of the methanol by distillation under reduced pressure, ...

Embodiment 3

[0022] (1) Preparation of 2-bromo-3-hydroxypyridine: Cool 60ml of 40% aqueous sodium hydroxide solution to -10-0°C with an ice-salt bath, and add 16g (0.1mol) of liquid bromine dropwise within this temperature range; Dissolve 9.8g (0.1mol) of 3-hydroxypyridine in 50ml of 40% aqueous sodium hydroxide solution, and then add this solution dropwise to the above liquid bromine solution, keeping the system temperature at 10°C; after the dropwise addition, stir at room temperature for 3 hours , and then adjust the pH to 7 with acid; the resulting crude product was recrystallized to obtain 2-bromo-3-hydroxypyridine with a yield of 70%.

[0023] (2) Preparation of 2-bromo-3-methoxypyridine: Add 0.7g of sodium to 40ml of methanol, heat the oil bath to reflux, keep the system reflux, dissolve 5g of 2-bromo-3-hydroxypyridine in 50ml of DMF , then added dropwise to the methanol solution of sodium; stirred for 15 minutes, removed most of the methanol by distillation under reduced pressure, ...

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Abstract

The invention belongs to the technical field of organic synthesis, and particularly relates to a preparation method of 2-bromine-3-methoxypyridine, which comprises the following reaction steps: (1) preparation of 2-bromine-3-hydroxypyridine, and (2) preparation of 2-bromine-3-methoxypyridine: cooling the sodium hydroxide aqueous solution to -10 DEG C to 0 DEG C by using an ice salt bath, and dropwise adding liquid bromine within the temperature range, dissolving 3-hydroxypyridine in a sodium hydroxide aqueous solution, dropwise adding the solution into the liquid bromine solution, and keepingthe system temperature at 10-15 DEG C, after dropwise adding, stirring the mixed solution for 2.5-3 hours at room temperature, and then adjusting the pH value to 7 by using acid; and recrystallizing the obtained crude product to obtain the 2-bromo-3-hydroxypyridine. The method has the beneficial effects of mild reaction conditions, short route and high yield.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a preparation method of 2-bromo-3-methoxypyridine. Background technique [0002] Pyridine and its derivatives are widely distributed in nature. Many plant components such as alkaloids contain pyridine ring compounds in their structures, which are the basis for the production of many important compounds, such as medicines, pesticides, dyes, surfactants, rubber additives, feed additives, food additives, adhesives, etc. Indispensable raw material in production. [0003] The existing method for preparing 2-bromo-3-methoxypyridine has a long synthetic route, harsh process conditions, low yield and troublesome post-treatment. Contents of the invention [0004] The purpose of the present invention is to overcome the technical deficiencies of long process route, harsh reaction conditions and low yield in the prior art, and provide a method of 2-bromo-3-methoxypyridine with ...

Claims

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Application Information

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IPC IPC(8): C07D213/65
CPCC07D213/65
Inventor 倪俊
Owner 常州传侑环保科技有限公司
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