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Preparation method of hydroxymethyl-substituted aromatic heterocyclic compound

A technology of aromatic heterocycle and hydroxymethyl group, which is applied in the fields of optoelectronics and organic semiconductor materials science, medicinal chemistry, and synthetic chemistry, can solve the problems of explosive hazardous chemicals and other problems, and achieve simple methods and avoid explosive hazardous chemicals and the effects of the use of precursor chemicals

Inactive Publication Date: 2020-07-24
安徽泽升科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In view of the shortcomings of the prior art described above, the object of the present invention is to provide a method for preparing a hydroxymethyl-substituted aromatic heterocyclic molecular building block, which is used to solve the need for the preparation of a hydroxymethyl-substituted aromatic heterocyclic ring in the prior art. Issues such as the use of explosive hazardous chemicals

Method used

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  • Preparation method of hydroxymethyl-substituted aromatic heterocyclic compound
  • Preparation method of hydroxymethyl-substituted aromatic heterocyclic compound
  • Preparation method of hydroxymethyl-substituted aromatic heterocyclic compound

Examples

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Embodiment 1

[0035] This embodiment provides the synthesis of 2-hydroxymethyl-5-nitrothiophene, the method is as follows:

[0036] Synthesis using borane dimethyl sulfide in tetrahydrofuran:

[0037] Under nitrogen protection, compound 5-nitrothiophene-2-carboxylic acid (0.86g, 4.97mmol) was added to dry tetrahydrofuran (10mL), and 1.0M borane tetrahydrofuran solution (14.8mL, 14.8mmol) was slowly added dropwise under ice-cooling , after the dropwise addition was completed, the temperature was raised to room temperature under the protection of nitrogen, and stirred for 16 hours. Add methanol 10mL under ice bath to quench, and extract with ethyl acetate (a total of 3 extractions, using 40mL ethyl acetate each time), combine the organic phases, wash with saturated sodium bicarbonate solution, water, saturated brine successively, anhydrous sulfuric acid Sodium-dried, filtered, and the filtrate was evaporated to dryness and purified by a rotary evaporator to obtain a brown oily substance, whi...

Embodiment 2

[0043] This embodiment provides the synthesis of 2-hydroxymethyl-5-nitrofuran, the method is as follows:

[0044] Under nitrogen protection, the compound 5-nitrofuran-2-carboxylic acid (1.00g, 6.37mmol) was added to dry tetrahydrofuran (12mL), and 1.0M borane tetrahydrofuran solution (19.2mL, 19.2mmol) was slowly added dropwise under ice-cooling , after the dropwise addition was completed, the temperature was raised to room temperature under the protection of nitrogen, and stirred for 16 hours. Add methanol 10mL under ice bath to quench, extract with ethyl acetate (40mL×3), combine the organic phases, wash with saturated sodium bicarbonate solution, water, saturated brine successively, dry over anhydrous sodium sulfate, filter, and the filtrate is evaporated by rotary evaporation After evaporation to dryness and purification, a brown oily substance, 2-hydroxymethyl-5-nitrofuran (0.89 g, yield 98%) was obtained.

[0045] m / z: 160.0[M+H]+HNMR: 1H-NMR (Bruker 400MHz, CDCl 3 ) δ...

Embodiment 3

[0050] This example provides the synthesis of 2-hydroxymethyl-3,5-dibromothiophene, which is synthesized using a THF solution of borane dimethyl sulfide, and the method is as follows:

[0051] Under nitrogen protection, compound 3,5-dibromothiophene-2-carboxylic acid (1.00g, 3.5mmol) was added into dry tetrahydrofuran (10mL), and 1.0M borane tetrahydrofuran solution (10.5mL, 10.5 mmol), after the dropwise addition was completed, the mixture was warmed up to room temperature and stirred for 16 hours under nitrogen protection. Add methanol 10mL under ice bath to quench, and extract with ethyl acetate (a total of 3 extractions, using 40mL ethyl acetate each time), combine the organic phases, wash with saturated sodium bicarbonate solution, water, saturated brine successively, anhydrous sulfuric acid Sodium-dried, filtered, and the filtrate was evaporated to dryness and purified by a rotary evaporator to obtain a light yellow oil, namely 2-(hydroxymethyl)-3,5-dibromothiophene (0.9...

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Abstract

The invention provides a preparation method of a hydroxymethyl-substituted aromatic heterocyclic compound, which comprises the following steps: in the presence of protective gas, dissolving aromatic heterocarboxylic acid in an aprotic solvent, adding a reducing agent in an ice bath, performing heating to room temperature, and performing reacting to obtain the hydroxymethyl-substituted aromatic heterocyclic compound. The yield of the hydroxymethyl substituted aromatic heterocyclic compound is 93% or above, the raw materials are cheap and easy to obtain, the method is simple, efficient and mildin reaction condition, and the defect that dangerous chemicals such as sodium borohydride which are prone to explosion are used in a conventional synthesis method can be overcome.

Description

technical field [0001] The invention relates to the fields of medicinal chemistry, synthetic chemistry, optoelectronics and organic semiconductor material science, and provides a simple and efficient preparation method for generating hydroxymethyl-substituted aromatic heterocyclic compounds by one-step reaction of aromatic heterocyclic carboxylic acids. The method is simple, efficient, and can avoid the use of explosive-prone hazardous chemicals such as sodium borohydride, and the nitro group in the substrate will not be reduced to amino. At the same time, the synthetic product can fill the blank of such products in domestic reagents and break through foreign or imported products. Price or technology monopoly for such products. Background technique [0002] Heterocyclic compounds (Heterocyclic compounds) are organic compounds containing aromatic heterocyclic structures in their molecules. Atoms constituting aromatic heterocycles contain at least one heteroatom in addition t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/44C07D307/71C07D333/28C07D307/56
CPCC07D307/56C07D307/71C07D333/28C07D333/44
Inventor 李展罗波孙文海孙喜玲宁芳贤
Owner 安徽泽升科技有限公司
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