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Preparation method of 2-bromo-5-iodobenzoic acid

A technology of bromobenzoic acid and iodobenzoic acid, applied in the field of preparation of 2-bromo-5-iodobenzoic acid, can solve problems such as only total yield, unsuitable for industrialized production, etc., achieves simple steps, good market prospects, and reaction mild conditions

Inactive Publication Date: 2018-02-09
SHANGHAI TWISUN BIO PHARM
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Problems solved by technology

Only disclose a kind of synthetic method taking o-bromobenzoic acid as starting raw material in the prior art, this method is made solvent with the concentrated sulfuric acid of 10 times of volume ratio, o-bromobenzoic acid and N-iodosuccinimide carry out The iodination reaction obtains the target product 2-bromo-5-iodobenzoic acid, but the total yield of this method is only about 60%, and a large amount of high-concentration waste acid is produced at the same time, which is not suitable for industrial production

Method used

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  • Preparation method of 2-bromo-5-iodobenzoic acid

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preparation example Construction

[0028] The invention provides a kind of preparation method of 2-bromo-5-iodobenzoic acid, comprises the steps:

[0029] (1) 5-amino-2-bromobenzoic acid, inorganic acid, organic solvent and water are mixed to obtain 5-amino-2-bromobenzoic acid mixed solution;

[0030] (2) adding the nitrite aqueous solution dropwise to the 5-amino-2-bromobenzoic acid mixed solution to undergo a diazonium reaction to obtain a diazonium salt system;

[0031] (3) Add the iodide aqueous solution dropwise to the diazonium salt system to generate iodine reaction;

[0032] (4) After the iodination reaction is completed, an aqueous solution of sodium bisulfite is added to the system for quenching to obtain 2-bromo-5-iodobenzoic acid.

[0033] The invention mixes 5-amino-2-bromobenzoic acid, inorganic acid, organic solvent and water to obtain 5-amino-2-bromobenzoic acid mixed liquid. In the present invention, the mass ratio of the 5-amino-2-bromobenzoic acid, inorganic acid, organic solvent and water ...

Embodiment 1

[0058] Add 200.0 g of m-aminobenzoic acid and 760.0 g of N,N-dimethylformamide in turn into the reaction flask. Stir and cool down to 0°C; slowly add 273.0g of N-bromosuccinimide, control the temperature at 0°C, and complete the addition within 1h. Incubate at 0°C for 1 h. After the reaction was completed, 3.4Kg of water was added dropwise to quench the reaction. After the drop was completed, stirring was continued at 10° C. for 1 h. Filter and wash the filter cake once with 400.0 g of water. The wet product was dried at 60°C for 10 h to obtain 261.0 g of 5-amino-2-bromobenzoic acid with a product yield of 82.8%.

[0059] The obtained 5-amino-2-bromobenzoic acid is carried out to NMR and mass spectrometry detection, the results are as follows:

[0060] 1 H NMR (400MHz, DMSO) δ13.05(s), 7.26(d, J=8.6Hz), 6.94(d, J=2.8Hz), 6.59(dd, J=8.6, 2.8Hz), 5.52(s) .

[0061] MS calcd for C 7 h 7 BrNO 2 (M+H) + :217,found:217.

[0062] NMR and mass spectrometric detection result...

Embodiment 2

[0069] 20.0Kg of m-aminobenzoic acid and 76.0Kg of N,N-dimethylacetamide were successively added into the reaction kettle. Stir and cool down to -10°C; slowly add 27.3Kg of liquid bromine, control the temperature at -10°C, and complete the addition in 2 hours. The reaction was incubated at -10°C for 2 hours. After the reaction was completed, 340.0Kg of water was slowly sucked in to quench the reaction, and after the dripping was completed, stirring was continued at 0°C for 1 hour. Centrifuge, and wash the filter cake once with 20.0Kg water. The wet product was dried at 60°C for 12 hours to obtain 25.6Kg of 5-amino-2-bromobenzoic acid with a yield of 81.3%.

[0070] The obtained 5-amino-2-bromobenzoic acid was detected by NMR and mass spectrometry, and the results showed that the target product 5-amino-2-bromobenzoic acid was obtained.

[0071] 37.5Kg of 98% sulfuric acid, 163.0Kg of water, 163.0Kg of tetrahydrofuran and 25.0Kg of prepared 5-amino-2-bromobenzoic acid were su...

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Abstract

The invention provides a preparation method of 2-bromo-5-iodobenzoic acid. The preparation method comprises the following steps: mixing 5-amino-2-bromobenzoic acid, inorganic acid, an organic solventand water to obtain 5-amino-2-bromobenzoic acid mixed liquid; (2) dropwise adding a nitrite aqueous solution into the 5-amino-2-bromobenzoic acid mixed liquid for carrying out diazo reaction to obtaina diazo salt system; (3) dropwise adding an iodizating agent aqueous solution into the diazo salt system for carrying out iodination reaction; (4) after the iodination reaction is finished, adding asodium hydrogen sulfite aqueous solution into the system for quenching to obtain the 2-bromo-5-iodobenzoic acid. According to the preparation method, the 5-amino-2-bromobenzoic acid is taken as a rawmaterial and is firstly subjected to diazotization, and diazotized diazo salt is then taken as a raw material and is subjected to the iodination reaction, so that the utilization rate of the 5-amino-2-bromobenzoic acid is greatly improved, and the yield of the 2-bromo-5-iodobenzoic acid is further increased.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of 2-bromo-5-iodobenzoic acid. Background technique [0002] 2-Bromo-5-iodobenzoic acid is an aromatic functional monomer with two different halogens and one carboxyl group. It can use the activity difference of each group to react with different groups to synthesize compounds substituted by various functional groups. It is widely used in medicine, metal organic chemistry and so on. For example, in the synthesis of anti-hepatitis C star drug velpatasvir, 2-bromo-5-iodobenzoic acid can be used as a raw material to synthesize its key intermediate. [0003] About the synthetic method of 2-bromo-5-iodobenzoic acid, there are few literature reports at present. Only disclose a kind of synthetic method taking o-bromobenzoic acid as starting raw material in the prior art, this method is made solvent with the concentrated sulfuric acid of 10 times of volum...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C245/20C07C51/363C07C63/68C07C227/16C07C229/58
CPCC07C245/20C07C51/363C07C227/16C07C63/68C07C229/58
Inventor 叶方国王其安叶敏徐佳发
Owner SHANGHAI TWISUN BIO PHARM
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