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Preparation method of 5-bromine-1,2,3-benzene tricarbonic acid

A technology of trimellitic acid and concentrated sulfuric acid, applied in the field of organic bromides and polycarboxylic acid aromatics, can solve the problems of complicated preparation method and long reaction time, and achieve the effects of simple reaction conditions, simple operation and good yield.

Active Publication Date: 2016-12-07
YANGZHOU UNIV
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  • Claims
  • Application Information

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Problems solved by technology

However, although the current preparation method of 5-bromo-1,2,3-benzenetricarboxylic acid has been reported, the preparation method is relatively complicated, and the reaction time is relatively long. Under the conditions of reaction, and then by reacting with acidic potassium permanganate to obtain the target product

Method used

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  • Preparation method of 5-bromine-1,2,3-benzene tricarbonic acid
  • Preparation method of 5-bromine-1,2,3-benzene tricarbonic acid
  • Preparation method of 5-bromine-1,2,3-benzene tricarbonic acid

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Effect test

Embodiment 1

[0020] The raw materials used for the synthesis of 5-bromo-1,2,3-benzenetricarboxylic acid are 1,2,3-benzenetricarboxylic acid, concentrated sulfuric acid, NBS (N-bromosuccinimide), and the mass of ice is 1.26 g, 18.4g, 1.28g, 10g.

Embodiment 2

[0022] The raw materials used for the synthesis of 5-bromo-1,2,3-benzenetricarboxylic acid are 1,2,3-benzenetricarboxylic acid, concentrated sulfuric acid, NBS (N-bromosuccinimide), and the mass of ice is 12.6 g, 184g, 12.8g, 100g.

Embodiment 3

[0024] The raw materials used for the synthesis of 5-bromo-1,2,3-benzenetricarboxylic acid are 1,2,3-benzenetricarboxylic acid, concentrated sulfuric acid, NBS (N-bromosuccinimide), and the mass of ice is 25.2 g, 368g, 25.6g, 200g.

[0025] The reaction formula of above technique is as follows:

[0026]

[0027] 2. Product verification

[0028] figure 1 It is the infrared spectrogram of the compound, the sample is pressed by KBr, and the measurement wavenumber range is 4000-400cm -1 . 1201cm -1 The stretching vibration of the C-O bond, 1492cm -1 、1579cm -1 The place is the vibration absorption peak of the benzene ring skeleton, 1729cm -1 The sharp peak is the stretching vibration peak of carboxyl carbonyl, 3093cm -1 is the stretching vibration peak of -OH on the carboxyl group, 3323cm -1 is the stretching vibration peak of -OH on the water molecule.

[0029] The crystal structure of the compound was determined by single crystal X-ray diffractometer. The SHELXTL...

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Abstract

The invention discloses a preparation method of 5-bromine-1,2,3-benzene tricarbonic acid and relates to the technical field of chemical synthesis of bromine base contained multi-carboxylic acid aromatics. The preparation method includes: subjecting 1,2,3-benzene tricarbonic acid and concentrated sulfuric acid and N-bromo-succinimide (NBS) to reaction by mixing and stirring; adding ice for refrigeration at the end of the reaction; filtering a mixture, taking solid phase of the mixture to clean with deionized water, and drying in vacuum and recrystalizing to obtain the 5-bromine-1,2,3-benzene tricarbonic acid. With the preparation, the 5-bromine-1,2,3-benzene tricarbonic acid can be prepared successfully, simpleness and moderation of process reaction conditions are achieved, large assisting equipment is avoided, simpleness in operation is achieved, yield of the reaction is good, and the overall yield can be up to 70%-80%.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis of organic bromides, especially polycarboxylic aromatic hydrocarbons containing bromine groups. Background technique [0002] Organobromides are important intermediates in organic synthesis and synthesis of drugs and pesticides, and have important applications in industry (leaded gasoline additives) and medicinal chemistry. The bromination of aromatic hydrocarbons is an important organic reaction in organic synthesis, and the brominated aromatic hydrocarbons produced are widely used. Not only can it be further converted into organometallic compounds to react with other types of compounds, but also can undergo a series of coupling reactions with alkenes, terminal alkynes, amines, halogenated aromatics and organometallic compounds. There are many methods for the preparation of organic bromides, such as the addition reaction of carbon-carbon unsaturated bonds and bromine molecules, and th...

Claims

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Application Information

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IPC IPC(8): C07C51/363C07C63/68
CPCC07C51/363C07C63/68
Inventor 刘文龙潘永梅杨芳
Owner YANGZHOU UNIV
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