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Preparation method of 4-bromo-2, 5-dichlorobenzoic acid

A technology of dichlorobenzoic acid and dichlorotoluene is applied in the preparation of carboxylates, the preparation of organic compounds, and the preparation of carboxylic acids by oxidation, which can solve problems such as non-marketable supply

Pending Publication Date: 2022-02-01
八叶草健康产业研究院厦门有限公司 +1
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Problems solved by technology

However, there are few reports on the synthesis method of 4-bromo-2,5-dichlorobenzoic acid and no commercial supply

Method used

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  • Preparation method of 4-bromo-2, 5-dichlorobenzoic acid
  • Preparation method of 4-bromo-2, 5-dichlorobenzoic acid
  • Preparation method of 4-bromo-2, 5-dichlorobenzoic acid

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preparation example Construction

[0027] The invention provides a kind of preparation method of 4-bromo-2,5-dichlorobenzoic acid, comprising the following steps:

[0028] (1) Mix 2,5-dichlorotoluene, a brominating reagent, a catalyst, and a first solvent to perform a bromination reaction to obtain 4-bromo-2,5-dichlorotoluene;

[0029] (2) Mix the 4-bromo-2,5-dichlorotoluene, the oxidizing agent and the second solvent, and carry out an oxidation reaction to obtain 4-bromo-2,5-dichlorobenzoic acid.

[0030] The invention mixes 2,5-dichlorotoluene, a bromination reagent, a catalyst and a first solvent to carry out a bromination reaction to obtain 4-bromo-2,5-dichlorotoluene. In the present invention, the brominated reagent is preferably hydrobromic acid, hypobromous acid, N-bromosuccinimide, bromooctane, liquid bromine, N-bromoacetamide, trimethylbromosilane, N -One or more of bromosuccinimide, 1,3-dibromo-5,5-dimethylhydantoin and benzyl ammonium tribromide. In the present invention, the molar ratio of the 2,5...

Embodiment 1

[0056] React according to the equation shown in formula I:

[0057]

[0058] Before the reaction, cool the reaction kettle to 5°C, add 30g of 2,5-dichlorotoluene solution, 200mL of dichloromethane and 2g of ferric chloride into the reaction kettle, start stirring, and in the stirring state at 0.1mL / min Add 10mL of N-bromosuccinimide dropwise to the solution at a rate of 1.5h, and the dropwise addition is completed in about 1.5h, during which the temperature is controlled not to exceed 7°C. After the addition was completed, the reaction was stirred at 5°C for 1 h. After the reaction was completed, the reaction solution was washed three times with water, and then washed three times with saturated sodium bicarbonate solution until the solution became colorless. The solution was separated with a separatory funnel to obtain 4- Organic solution of bromo-2,5-dichlorotoluene. Anhydrous sodium sulfate was added to the solution for drying, and the organic solvent was removed by rota...

Embodiment 2

[0063] React according to the equation shown in formula II:

[0064]

[0065] Before the reaction, cool the reactor to 3°C, add 16g of 2,5-dichlorotoluene solution, 100mL of acetonitrile and 1g of iron into the reactor, start stirring, and pour the solution into the solution at a rate of 0.3mL / min under stirring. 5.5mL hypobromous acid was added dropwise to the solution, and the dropwise addition was completed in about 1 hour, during which the temperature was controlled not to exceed 5°C. After the addition was completed, the reaction was stirred at 3°C ​​for 1.5 h. After the reaction was completed, the reaction solution was washed three times with water, and then washed three times with saturated sodium bicarbonate solution until the solution became colorless. The solution was separated with a separatory funnel to obtain 4 - Organic solution of bromo-2,5-dichlorotoluene. Solid calcium oxide was added to the solution for drying, and the organic solvent was removed by rotar...

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Abstract

The invention provides a preparation method of 4-bromo-2, 5-dichlorobenzoic acid, and belongs to the technical field of organic synthesis. The preparation method comprises the following steps: (1) mixing 2, 5-dichlorotoluene, a bromination reagent, a catalyst and a first solvent, and carrying out a bromination reaction to obtain 4-bromo-2, 5-dichlorotoluene; and (2) mixing the 4-bromo-2, 5-dichlorotoluene, an oxidant and a second solvent, and carrying out an oxidation reaction to obtain the 4-bromo-2, 5-dichlorobenzoic acid. According to the invention, 2, 5-dichlorotoluene is taken as an original raw material which is cheap and easy to obtain, 4-bromo-2, 5-dichlorobenzoic acid can be prepared with high yield and high purity by sequentially carrying out bromination reaction and oxidation reaction, and the method is simple and suitable for industrial production. The result of the embodiment shows that the yield of the 4-bromo-2, 5-dichlorobenzoic acid obtained by the method disclosed by the invention is 91-94.9%, and the purity of the 4-bromo-2, 5-dichlorobenzoic acid is 98-98.7%.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of 4-bromo-2,5-dichlorobenzoic acid. Background technique [0002] Heart failure, a disease with a high mortality rate, has become one of the current public health problems worldwide. At present, the clinical preparation methods for heart failure mainly use diuretics, vasodilators, etc. to reduce excessive blood volume to improve the clinical symptoms of patients with heart failure, but long-term use of diuretics may cause hyponatremia and increase the risk of death of patients . [0003] Arginine vasopressin is a cyclic nonapeptide hormone released from the posterior pituitary gland in response to changes in plasma tone, decreased plasma volume, or changes in blood pressure, and plays an important role in cardiomyocyte apoptosis and the neuro-endocrine system. If its content is too high, it is easy to stimulate the V2 receptor on the surface of t...

Claims

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Application Information

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IPC IPC(8): C07C51/16C07C51/285C07C63/70
CPCC07C51/16C07C51/285C07C63/70
Inventor 汤须崇赵应伟谢嘉斌邓爱华
Owner 八叶草健康产业研究院厦门有限公司
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