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The synthetic method of 2-hydroxynaphthalene-1-boronic acid

A synthesis method and technology of hydroxynaphthalene are applied in the field of synthesis and purification of high-purity intermediate 2-hydroxynaphthalene-1-boronic acid, can solve problems such as instability of target product, achieve high yield, simple process steps, and process steps easy effect

Active Publication Date: 2021-10-29
棓诺(苏州)新材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] In actual operation, it is found that in the final hydrolysis deprotection reaction, under acidic conditions, the target product is very unstable, and it is very easy to undergo deboration and be converted into raw material 2-naphthol, and only less than 5% of the target product can be obtained.

Method used

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  • The synthetic method of 2-hydroxynaphthalene-1-boronic acid
  • The synthetic method of 2-hydroxynaphthalene-1-boronic acid
  • The synthetic method of 2-hydroxynaphthalene-1-boronic acid

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Embodiment 1

[0058] Embodiment 1, a kind of synthetic method of 2-hydroxynaphthalene-1-boronic acid, carries out following steps successively:

[0059] 1), the synthesis of 1-bromo-2-naphthol (using 2-naphthol and NBS to react synthetic 1-bromo-2-naphthol in solvent):

[0060]Add 144.2g of 2-naphthol (1mol) and 280ml of DMF (dimethylformamide) into a 1000ml reaction flask, stir evenly (stirring time is about 10 minutes), cool down to 0-5°C, and then add dropwise (dropwise Adding time is about 20 to 30 minutes) 178g NBS (N-bromosuccinimide, 1mol), using a water bath to control the temperature of the solution in the reaction bottle does not exceed 5 ° C, after the addition is completed, keep it warm at 0-5 ° C for 20 Minutes, adopt HPLC to monitor at this moment, raw material 2-naphthol is less than 1%.

[0061] Add 500ml of water to the liquid in the reaction bottle, quench (thereby the end of the reaction), then add 200ml of toluene, separate layers, the organic layer is located in the up...

Embodiment 3-1

[0075] Change the triisopropyl borate 1.8mol in the embodiment 1 step 3) into tributyl borate 1.9mol, and the rest are equal to the step 3) of the embodiment 1;

[0076] 118 g (0.58 mol) of off-white powder 2-methoxynaphthalene-1-boronic acid was obtained, with a content of 99.7% and a yield of 58%.

Embodiment 3-2

[0078] Change the triisopropyl borate 1.8mol in step 3) of embodiment 1 into trimethyl borate 2.0mol, and the rest are equal to step 3) of embodiment 1;

[0079] 119 g (0.59 mol) of off-white powder 2-methoxynaphthalene-1-boronic acid was obtained, with a content of 99.5% and a yield of 58.6%.

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Abstract

The invention discloses a synthesis method of 2-hydroxynaphthalene-1-boronic acid, which comprises the following steps: 1), synthesis of 1-bromo-2-naphthol; 2), protection of hydroxy alkylation: sodium hydrogen, containing 1 The mixed solution of bromo-2-naphthol and dimethyl sulfate are subjected to heat preservation reaction to obtain 1-bromo-2-methoxynaphthalene; 3), bromo-position boronic acid substitution: 1-bromo-2-methoxy Naphthalene, borates, n-butyllithium, etc. carry out insulation reaction to obtain 2-methoxynaphthalene-1-boronic acid; 4), demethylation reaction: 2-methoxynaphthalene-1-boronic acid, boron tribromide reaction After post-treatment, 2-hydroxy-naphthalene-1-boronic acid is obtained. The method of the invention can obtain a single high-purity, high-yield target product, effectively solving the problem of instability in the preparation process of 2-hydroxy-naphthalene-1-boronic acid.

Description

technical field [0001] The invention relates to a method for synthesizing organic matter, in particular to a method for synthesizing and refining a high-purity intermediate 2-hydroxynaphthalene-1-boronic acid. Background technique [0002] 2-Hydroxynaphthalene-1-boronic acid is an organic compound intermediate that can be used in OLED materials, medicine and pesticide industries. Since its synthesis method is less disclosed in the prior art, commercially available high-purity 2-hydroxynaphthalene-1-boronic acid is rare and expensive. [0003] In the literature, 2-naphthol is used as a raw material, and it is realized by a three-step reaction (such as formula 1) of hydroxyl etherification protection, boration and hydrolysis deprotection, but more than 90% of the detected product is 2-hydroxynaphthalene-3-boronic acid. rather than the target product. This is because the energy levels at different sites of 2-naphthol are different, and the boronic acid group is more likely to...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02
CPCC07F5/025
Inventor 李显跃宋文志吴清来郭磊傅春荣余鹏
Owner 棓诺(苏州)新材料有限公司