Preparation method of 2, 4, 6-tribromoaniline
By adding aniline to a mixed solution of water and bromide and adding hydrogen peroxide solution dropwise, the synthesis efficiency and purity of 2,4,6-tribromobronomicline was successfully improved, and the problems of low yield and low purity in the prior art were solved. , realizes an efficient and environmentally friendly synthesis process.
Patent Information
- Application Number
- CN202411856762.1
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2024-12-17
- Publication Date
- 2025-02-18
AI Technical Summary
The existing 2,4,6-tribromobronoiline synthesis methods have problems such as low yield and low purity, which limits its large-scale application.
Aniline was added to the mixed solution of water and bromide, and the hydrogen peroxide solution was added dropwise. After incubation reaction for 1 to 10 hours, it was then filtered, washed and dried in vacuo to obtain 2,4,6-tribromobronoiline as a white solid.
This method is simple to operate, has high yield, and meets quality requirements. It solves the problem of using a large amount of bromine and realizes an efficient and environmentally friendly synthesis process.
Smart Images
Figure CN119462396A_ABST
Abstract
Description
Technical Field
[0001] The invention belongs to the technical field of organic synthesis, and specifically relates to a method for preparing 2,4,6-tribromoaniline. Background Art
[0002] 2,4,6-tribromoaniline is an important organic compound with a wide range of applications. However, the existing synthesis methods have problems such as low yield and low purity, which restrict the large-scale application of 2,4,6-tribromoaniline. Therefore, developing an efficient and environmentally friendly synthesis method and a corresponding purification process is of great significance for expanding the application field of 2,4,6-tribromoaniline. Summary of the invention
[0003] In order to solve the above technical problems, the present invention provides a method for preparing 2,4,6-tribromoaniline, which has ingenious design and perfect and reasonable process.
[0004] The technical solution of the present invention: A preparation method of 2,4,6-tribromoaniline comprises the following steps: adding aniline to a mixed solution of water and bromide, stirring, then dripping a hydrogen peroxide solution into the mixture, and keeping the mixture warm for 1 to 10 hours; precipitating a solid, filtering the mixture, washing the filter cake with a small amount of water, collecting the obtained white solid TBA, and drying it at 20 to 60 degrees Celsius in vacuum for 24 hours; the bromide is one of hydrogen bromide, sodium bromide and potassium bromide; and the solvent is one of water, methanol and ethanol.
[0005] The bromide is preferably hydrogen bromide.
[0006] The solvent is preferably water.
[0007] The reaction temperature is preferably 30-40°C.
[0008] The reaction time is preferably 4 to 7 hours.
[0009] The invention has the advantages of using aniline as a starting material, oxidizing a bromination reagent through hydrogen peroxide, and then bromination synthesis; the problem of using a large amount of bromine is solved; the method is reasonable and simple, easy to operate, high in yield, and the purity meets the quality research requirements. BRIEF DESCRIPTION OF THE DRAWINGS
[0010] Figure 1 It is an operation flow chart of the present invention. DETAILED DESCRIPTION
[0011] See attached Figure 1 All features disclosed in this specification, or steps in all methods or processes disclosed, except for mutually exclusive features and / or steps, can be combined in any way. Example
[0012] Aniline (9.3 g, 0.10 mol) was added to a mixed solution of hydrobromic acid (47%, 51.6 g, 0.30 mol) and water (200 ml), stirring was started, and H202 solution (28%, 36.4 g, 0.30 mol) was added dropwise later, and the mixture was kept at 30-40°C for 6 hours. The solid was precipitated, the mixture was filtered, the filter cake was washed with a small amount of water, and the obtained white solid TBA was collected. It was dried at 60°C in vacuum for 24 hours, and the GC purity was 99.5%, and the yield was 96%. Example
[0013] Aniline (9.3 g, 0.10 mol) was added to a mixed solution of water (200 ml) and sodium bromide (30.8 g, 0.30 mol) and stirred. Then, H202 aqueous solution (28%, 36.4 g, 0.30 mol) was added dropwise to the mixture and continued at 40-50°C for 6 hours. The solid was precipitated, the mixture was filtered, the filter cake was washed with a small amount of water, and the obtained white solid TBA was collected. It was dried at 60°C in vacuum for 24 hours. The GC purity was 96.8% and the yield was 88%. Example
[0014] Aniline (9.3 g, 0.10 mol) was added to a mixed solution of water (220 ml) and potassium bromide (35.7 g, 0.30 mol) and stirred. Then, H202 aqueous solution (28%, 36.4 g, 0.30 mol) was added dropwise to the mixture and continued at 50-70°C for 6 hours. The solid was precipitated, the mixture was filtered, the filter cake was washed with a small amount of water, and the obtained white solid TBA was collected. It was dried at 60°C in vacuum for 24 hours. The GC purity was 93.5% and the yield was 86%.
[0015] 2,4,6-Tribromoaniline is an important intermediate for the preparation of 1,3,5-trimethoxybenzene (TMB), and its structure is as follows: ; ; 1,3,5-Trimethoxybenzene (TMB) is a white crystalline powder, insoluble in water, and is an important organic synthesis intermediate. It is mainly used in the fields of pharmaceutical manufacturing and pesticide synthesis, and is an important raw material for the synthesis of buflomedil, a new dilator drug for peripheral vascular disorders.
Claims
1. A method for preparing 2,4,6-tribromoaniline, characterized in that: Aniline is added to a mixed solution of water and bromide, and stirred. Then, a hydrogen peroxide solution is added dropwise to the mixture, and the mixture is kept warm for 1 to 10 hours. Solid is precipitated, the mixture is filtered, and the filter cake is washed with a small amount of water. The obtained white solid TBA is collected and dried at 20°C to 60°C in vacuum for 24 hours. The bromide is one of hydrogen bromide, sodium bromide, and potassium bromide. The solvent is one of water, methanol, and ethanol.
2. The method for preparing 2,4,6-tribromoaniline according to claim 1, characterized in that: The bromide is preferably hydrogen bromide.
3. The method for preparing 2,4,6-tribromoaniline according to claim 1, characterized in that: The solvent is preferably water.
4. The method for preparing 2,4,6-tribromoaniline according to claim 1, characterized in that: The reaction temperature is 30-40°C.
5. The method for preparing 2,4,6-tribromoaniline according to claim 1, characterized in that: The reaction time is 4 to 7 hours.
6. The method for preparing 2,4,6-tribromoaniline according to claim 1, characterized in that: Synthesis reaction equation: Main reaction: Aniline Hydrobromic Acid Hydrogen Peroxide TBA Or Aniline Sodium Bromide Hydrogen Peroxide TBA Or Aniline, potassium bromide, hydrogen peroxide, TBA.