Synthesis method for 2-hydroxy naphthalene-1-boracic acid

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

Active Publication Date: 2019-02-05
棓诺(苏州)新材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • Synthesis method for 2-hydroxy naphthalene-1-boracic acid
  • Synthesis method for 2-hydroxy naphthalene-1-boracic acid
  • Synthesis method for 2-hydroxy naphthalene-1-boracic acid

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Experimental program
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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 for 2-hydroxy naphthalene-1-boracic acid. The synthesis method comprises the following steps: 1) synthesizing 1-bromo-2-naphthol; 2) carrying out hydroxy alkylation protection: carrying out thermal insulation reaction on sodium hydrogen, mixed liquid containing 1-bromo-2-naphthol and dimethyl sulfate to obtain 1-bromo-2-methoxynaphthalene; 3) carrying outbromo-boracic acid base substitution: carrying out thermal insulation reaction on 1-bromo-2-methoxynaphthalene, boracic acid ester, n-butyllithium and the like to obtain 2-methoxy naphthalene-1-boracic acid; 4) carrying out demethylation reaction: after the 2-methoxy naphthalene-1-boracic acid and boron tribromide react, carrying out post-processing to obtain the 2-hydroxy-naphthalene-1-boracic acid. According to the method disclosed by the invention, a single high-purity and high-yield target product can be obtained, and the problem of instable preparation process of the 2-hydroxy-naphthalene-1-boracic acid is effectively solved.

Description

Technical field [0001] The present invention relates to a method for synthesizing organic substances, and 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, pharmaceutical and pesticide industries. Since its synthesis method is rarely 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 raw material, and is realized through a three-step reaction of hydroxyl etherification protection, boration and hydrolysis deprotection (such as formula 1). However, more than 90% of the product has been tested to be 2-hydroxynaphthalene-3-boric acid. rather than the target product. This is because the energy levels at different positions of 2-naphthol are different. Dur...

Claims

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Application Information

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Patent Type & Authority Applications(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
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