Method for synthesizing 3-hydroxy biphenyl

A technology of hydroxybiphenyl and synthesis method, which is applied in chemical instruments and methods, magnesium organic compounds, preparation of organic compounds, etc., can solve the problems of cumbersome processing, high cost, expensive, etc., and meet the requirements of simple reaction equipment and easy control of reaction , the effect of mild reaction conditions

Inactive Publication Date: 2019-05-24
SHANGHAI JINGCHUN BIOCHEM TECH CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The synthetic research of 3-hydroxybiphenyl has been reported in many domestic and foreign literatures, generally using Suzuki coupling reaction, that is, in alkali (K 2 CO 3 、K 3 PO 4 , NaOH, etc.) under the action of palladium catalysis (Pd(PPh 3 ) 4 or PdCl 2 (PPh 3 ) 2 ) of organic aromatic borides (3-hydroxyphenylboronic acid or phenylboronic acid) and hal

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  • Method for synthesizing 3-hydroxy biphenyl
  • Method for synthesizing 3-hydroxy biphenyl

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Embodiment 1

[0030] This embodiment provides a process for synthesizing 3-hydroxybiphenyl, and the specific synthesis steps are as follows:

[0031] (1) prepare 10L glass reactor, N 2 protection, adding magnesium scraps (171g, 7.12mol) and 800ml solvent THF in sequence, then heating to 62-64°C, adding dropwise a THF (2L) solution of 3-bromoanisole (1.27kg, 6.78mol) to keep a slight Add dropwise under boiling conditions. After the dropwise addition, mature at 62-65°C for 1 hour to react 3-bromoanisole with magnesium chips to obtain Grignard reagent;

[0032] (2) Cool the Grignard reagent prepared in step (1) to 5-10°C in an ice-water bath, and then add the catalyst dpppNiCl first 2 (3.5g, 6.45mmol), then add bromobenzene (845g, 5.38mol) dropwise, the rate of addition is controlled within 1.0-1.5h, after the dropwise addition, first react at an internal temperature of 40°C for 1h, then reflux at 68°C for 3h; After the reaction, cool the reaction solution to 5-10°C, add 600ml concentrated h...

Embodiment 2

[0040] This embodiment provides a process for synthesizing 3-hydroxybiphenyl, and the specific synthesis steps are as follows:

[0041] (1) prepare 10L glass reactor, N 2 protection, adding magnesium chips (179g, 7.46mol) and 800ml solvent THF in sequence, then heating to 62-64°C, adding dropwise a THF (2L) solution of 3-bromoanisole (1.27kg, 6.78mol) to keep a slight Add dropwise under boiling conditions. After the dropwise addition, mature at 62-65°C for 1 hour to react 3-bromoanisole with magnesium chips to obtain Grignard reagent;

[0042] (2) Cool the Grignard reagent prepared in step (1) to 5-10°C in an ice-water bath, and then add the catalyst dpppNiCl first 2 (3.5g, 6.45mmol), then added dropwise bromobenzene (1064g, 6.78mol), the rate of addition was controlled within 1.5-2.0h, after the dropwise addition, the internal temperature was first reacted at 40°C for 1h, and then refluxed at 68°C for 3h; After the end, cool the reaction solution to 5-10°C, add 600ml concen...

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Abstract

The invention discloses a method for synthesizing 3-hydroxy biphenyl, which is characterized by comprising the following steps of: under the protection of inert gas or N2 gas, using THF as a solvent,reacting bromoanisole with magnesium scraps to obtain a Grignard reagent; reacting Grignard reagent with bromobenzene in the presence of a catalyst dpppNiCl2, adding an acid solution for quenching reaction, layering, extracting water phase, separating liquid, combining the obtained organic phases, washing, drying, concentrating, and distilling to obtain an intermediate 3-methoxybiphenyl; adding the 3-methoxybiphenyl into glacial acetic acid, adding a 48% HBr solution, heating, refluxing, aging, cooling, extracting and separating, mixing the obtained organic phases, washing, drying, concentrating, and recrystallizing toluene to obtain the 3-hydroxy biphenyl. The method has the advantages of convenient operation, easy control of reaction and simple requirement on reaction equipment, the whole process is suitable for industrial production, and the GC purity of the prepared 3-hydroxy biphenyl can reach more than 99%, and the total yield is more than 60%.

Description

technical field [0001] The invention relates to a method for high-purity 3-hydroxybiphenyl, which belongs to the technical field of synthesis of new organic materials and application of pharmaceutical intermediates. Background technique [0002] 3-Hydroxybiphenyl is an important fine organic chemical product and organic intermediate. It has a wide range of uses including food antiseptic and sterilization, synthesis of printing and dyeing auxiliaries, synthesis of heat-stable materials, preparation of new flame retardants, etc., as well as application in the development and research of new pharmaceuticals middle. In recent years, with the continuous development of economy and science and technology, the market demand for 3-hydroxybiphenyl has increased year by year. Therefore, it is very important to develop a method for synthesizing high-purity 3-hydroxybiphenyl and realizing industrialization. [0003] The synthetic research of 3-hydroxybiphenyl has been reported in many ...

Claims

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Application Information

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IPC IPC(8): C07C39/15C07C37/055C07F3/02C07C43/205C07C41/30
Inventor 阚洪柱姜苏徐久振
Owner SHANGHAI JINGCHUN BIOCHEM TECH CO LTD
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