Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Method for preparing 3-bromo-4-methoxyaniline

A technology of methoxyaniline and methoxynitrobenzene, applied in the production field of pharmaceutical intermediates, can solve the problems of less 3-bromo-4-methoxyaniline, unsuitable for industrial production, and difficult to industrial production. Achieve the effect of convenient post-processing, low price and convenient processing

Active Publication Date: 2011-09-28
溧阳常大技术转移中心有限公司
View PDF4 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The raw materials of this method are chlorine-containing compounds, and the price is expensive. The solvent uses flammable and explosive ether with a low boiling point, which has great potential safety hazards and is difficult to carry out industrial production.
[0006] In summary, there are few reports on the related synthesis methods of 3-bromo-4-methoxyaniline, and none of them are suitable for industrial production.

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
  • Method for preparing 3-bromo-4-methoxyaniline

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] (1) Bromination reaction: Add 7.05 g of p-fluoronitrobenzene and 25 g of acetic acid into the reaction vessel, and control the temperature of the water bath to 15 °C. 9.34 g of N-bromosuccinimide were added slowly with stirring. During the addition, the temperature should not exceed 15°C. After the addition, the reaction was incubated for 10 h, and the reaction ended. After the reaction, the reactant was poured into 500 ml of ice water, and the solid was precipitated, filtered with suction, and dried to obtain 9.95 g of 3-bromo-4-fluoronitrobenzene as a light yellow powder solid, with a yield of 90.5%.

[0024] (2) Etherification reaction: add 11.0 g of 3-bromo-4-fluoronitrobenzene and 175 ml of methanol to the reaction vessel, control the temperature in a water bath at 10 °C, slowly add 12.15 g of sodium methoxide, and keep the system temperature at 10°C. After the addition, the reaction was incubated for 4 h, and the reaction ended. After the reaction was complete...

Embodiment 2

[0027] (1) Bromination reaction: Add 7.05 g of p-fluoronitrobenzene and 25 g of acetic acid to the reaction vessel, and control the temperature of the water bath to 25 °C. 9.34 g of N-bromosuccinimide were added slowly with stirring. During the addition process, the temperature should not exceed 25°C. After the addition, the reaction was incubated for 4.5 h, and the reaction ended. After the reaction was completed, the reactant was poured into 500 ml of ice water to precipitate a solid, which was filtered by suction and dried to obtain 9.98 g of 3-bromo-4-fluoronitrobenzene as a light yellow powder solid, with a yield of 90.7%.

[0028] (2) Etherification reaction: add 11.0 g of 3-bromo-4-fluoronitrobenzene and 175 ml of methanol to the reaction vessel, control the temperature in a water bath at 20 °C, slowly add 12.15 g of sodium methoxide, and keep the system temperature at 20°C. After the addition, the reaction was incubated for 0.8 h, and the reaction ended. After the ...

Embodiment 3

[0031] (1) Bromination reaction: Add 7.05 g of p-fluoronitrobenzene and 25 g of acetic acid into the reaction vessel, and control the temperature of the water bath to 35 °C. 9.34 g of N-bromosuccinimide were added slowly with stirring. During the addition process, the temperature should not exceed 35°C. After the addition, keep the temperature for 2.0 h to complete the reaction. After the reaction, the reactant was poured into 500 ml of ice water, and the solid was precipitated, filtered with suction, and dried to obtain 9.95 g of 3-bromo-4-fluoronitrobenzene as a light yellow powder solid, with a yield of 90.5%.

[0032] (2) Etherification reaction: add 11.0 g of 3-bromo-4-fluoronitrobenzene and 175 ml of methanol to the reaction vessel, control the temperature in a water bath at 40 °C, slowly add 12.15 g of sodium methoxide, and keep the system temperature at 40°C. After the addition, the reaction was incubated for 0.8 h, and the reaction ended. After the reaction was co...

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 relates to the field of organic synthesis, in particular to a method for preparing 3-bromo-4-methoxyaniline. The method for industrially preparing 3-bromo-4-methoxyaniline comprises the step of: by taking p-nitrochlorobenzene as an initial raw material, synthesizing 3-bromo-4-methoxyaniline through three-step reactions of bromization, etherification and nitro-reduction. The 3-bromo-4-methoxyaniline obtained in the process is yellow powdery solid with the purity of 99.9 percent, the raw material conversion rate at each step respectively reaches 100 percent, and the overall yield rate throughout the whole process reaches 62 percent.

Description

technical field [0001] The present invention relates to a kind of production method of pharmaceutical intermediate, specifically, the present invention is a kind of preparation method of 3-bromo-4-methoxyaniline. Background technique [0002] At present, 3-bromo-4-methoxyaniline has been found to be widely used in medicine. 3-Bromo-4-methoxyaniline can be used to prepare analogs of anticancer drug Combretastatin A-4, a drug that replaces cell cycle checkpoint kinase 1 (CHK1), and treats obesity and the body Drugs for disorders, drugs with Src kinase inhibitory activity, drugs that can replace tyrosine kinase inhibitors, drugs that replace endo-β-glucuronidase heparanase inhibitors, polycystic kidney disease, colon polyps, Drugs for cancer, stroke in mammals, drugs for the inhibition of smooth muscle cell proliferation, synthesis of sulfonamides with antimicrobial properties. [0003] At present, 3-bromo-4-methoxyaniline mainly contains the following two synthetic methods: ...

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
Patent Type & Authority Applications(China)
IPC IPC(8): C07C217/84C07C213/02
Inventor 陈兴权牛纪胜董燕敏丁明杰卿鹏程
Owner 溧阳常大技术转移中心有限公司
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products