Unlock instant, AI-driven research and patent intelligence for your innovation.

Synthesis method of 2-bromomalonaldehyde

A technology of bromomalonaldehyde and a synthesis method, applied in the field of synthesis of 2-bromomalonaldehyde, can solve the problems of restricting the industrial production of 2-bromomalonaldehyde, low product purity, unstable product and the like, and achieves good industrial application Prospect, the effect of high product yield and few steps

Inactive Publication Date: 2020-03-17
苏州诚和医药化学有限公司
View PDF5 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] This synthetic method needs to be heated, and hydrochloric acid will be removed in post-treatment process, and product is unstable, and reaction yield is low, generally no more than 60%, and product purity is low, seriously restricts the industrialized production of 2-bromomalondialdehyde

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Synthesis method of 2-bromomalonaldehyde
  • Synthesis method of 2-bromomalonaldehyde
  • Synthesis method of 2-bromomalonaldehyde

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] The synthetic method of 2-bromomalondialdehyde comprises the following steps:

[0025] Add 5g (32mmol) of 2-bromo-1,3-propanediol, 20ml of water, 2.7g (32mmol) of sodium carbonate, and 0.1g of TEMPO into the reaction flask, and cool it to -5°C in a salt bath, and add fresh Add 6g (80mmol) of 10% sodium hypochlorite, stir and keep warm at -5 to 0°C for 3 hours after adding, adjust the pH to 2-3 with 2M hydrochloric acid, cool to -5 to 0°C, filter to obtain 4.15g of 2-bromomalonaldehyde, and collect The yield is 86%, and the purity is 99.85% as detected by HPLC. HPLC conditions: Mobile phase: 800ml water; 200ml acetonitrile. Detection wavelength: 254nm, flow rate 1.0ml / min, sample 0.01g, diluted to 25ml with mobile phase, injection volume 5μl.

Embodiment 2

[0027] The synthetic method of 2-bromomalondialdehyde comprises the following steps:

[0028] 10g (64mmol) of 2-bromo-1,3-propanediol, 40ml of water, 6.9g (64mmol) of sodium carbonate and 0.1g of TEMPO were added to the reaction flask, and cooled to 0°C in a salt bath, and fresh 10% Sodium hypochlorite 12g (160mmol), after adding, stir and keep warm at -5 to 0°C for 3 hours, adjust pH to 2-3 with 2M hydrochloric acid, cool to -5 to 0°C, filter to obtain 8.0g of 2-bromomalonaldehyde, yield 83 %, HPLC content 99.91%. HPLC conditions: Mobile phase: 800ml water; 200ml acetonitrile. Detection wavelength: 254nm, flow rate 1.0ml / min, sample 0.01g, diluted to 25ml with mobile phase, injection volume 5μl.

Embodiment 3

[0030] The synthetic method of 2-bromomalondialdehyde comprises the following steps:

[0031] 10g (64mmol) of 2-bromo-1,3-propanediol, 40ml of water, 6.9g (64mmol) of sodium carbonate, and 0.1g of TEMPO were added to the reaction flask, cooled to -10°C in a salt bath, and fresh 10 % sodium hypochlorite 12g (160mmol), after adding, stir and keep warm at -5 to 0°C for 2 hours, adjust the pH to 2-3 with 2M hydrochloric acid, cool to -5 to 0°C, filter to obtain 7.68g of 2-bromomalonaldehyde, the yield 79%, HPLC content 99.57%. HPLC conditions: mobile phase: 800ml water; acetonitrile 200ml. Detection wavelength: 254nm, flow rate 1.0ml / min, sample 0.01g, diluted to 25ml with mobile phase, injection volume 5μl.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a synthesis method of 2-bromomalonaldehyde. The preparation method comprises the following steps: taking 2-bromo-1,3-propylene glycol as a raw material and water as a solvent,adding a catalytic amount of 2,2,6,6-tetramethylpiperidine-nitroxide under an alkaline condition, dropwise adding sodium hypochlorite at a low temperature, carrying out cooling crystallization, and performing filtration to obtain 2-bromomalondialdehyde with the purity of above 99%. The synthesis method for obtaining the target compound by oxidizing alcohol into aldehyde through a one-step technology with sodium hypochlorite via taking TEMPO as a catalyst has the advantages of mild reaction conditions, good product quality, high yield, and simplicity in operation.

Description

technical field [0001] The invention belongs to the technical field of medicine synthesis and relates to a synthesis method of 2-bromomalondialdehyde. [0002] technical background [0003] 2-Bromomalonaldehyde, also known as bromomalonaldehyde, is the main intermediate in the synthesis of heterocyclic compounds such as pyrimidine and imidazole, and is widely used in the synthesis of liquid crystals and the synthesis of some raw materials. Its chemical structure is as follows: [0004] [0005] The synthesis method in the prior art uses 1,1,3,3-tetramethoxypropane as raw material, after deprotection, bromination and concentration to obtain the target compound, the synthesis route is as follows: [0006] [0007] The synthesis method needs heating, and hydrochloric acid needs to be removed in the post-treatment process, the product is unstable, the reaction yield is low, generally not more than 60%, and the product purity is low, which seriously restricts the industrial...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07C45/30C07C47/14
CPCC07C45/30
Inventor 陈晓强方欢
Owner 苏州诚和医药化学有限公司