Method for synthesizing 4,4'-dibromo p-terphenyl

A technology for para-terphenyl and terphenyl, applied in chemical instruments and methods, preparation of halogenated hydrocarbons, organic chemistry, etc., can solve problems such as increasing costs, and achieve the effect of reducing costs and simplifying post-processing procedures

Active Publication Date: 2018-07-27
XUZHOU B&C CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These methods with higher yields require additional addition of catalysts, increasing the cost of synthesis

Method used

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  • Method for synthesizing 4,4'-dibromo p-terphenyl
  • Method for synthesizing 4,4'-dibromo p-terphenyl

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Add 100g of terphenyl and 1L of bromobenzene into a 2L reaction flask, add 174g of liquid bromine under stirring, and then raise the temperature to 105°C for 40 hours of reaction. Using low temperature (-10-0°C) condensation, at least part of the Br produced by heating terphenyl and liquid bromine 2 The steam is condensed and refluxed to the reaction bottle, and at least part of the Br 2 and hydrogen bromide vapors are absorbed using water.

[0044] After cooling to 25°C, pour the reaction solution of terphenyl and liquid bromine into 2L of methanol, stir for 0.5 hour, filter, and wash the filter cake at least once with 800mL of methanol. After filtering, the filter cake was dried at 60° C. for 2 hours in a blast oven. The dried crude product was added to 200mL toluene for reflux and beating for 12 hours. After hot filtration, the filter cake was rinsed once with 200mL toluene and then sucked dry. Add the drained filter cake to 200 mL of toluene and reflux for beatin...

Embodiment 2

[0046] In a first example, 4,4'-dibromo-p-terphenyl was prepared by the following method:

[0047] Add 100g of terphenyl and 1L of bromobenzene into a 2L reaction flask, add 174g of liquid bromine under stirring, and then raise the temperature to 100°C for 40 hours to react. Using low temperature (-10-0°C) condensation, at least part of the Br produced by heating terphenyl and liquid bromine 2 The steam is condensed and refluxed to the reaction bottle, and at least part of the Br 2 and hydrogen bromide vapors are absorbed using water.

[0048] After cooling to 25°C, pour the reaction solution of terphenyl and liquid bromine into 2L of methanol, stir for 0.5 hour, filter, and wash the filter cake at least once with 800mL of methanol. After filtering, the filter cake was dried at 60° C. for 2 hours in a blast oven. The dried crude product was added to 200mL toluene for reflux and beating for 12 hours. After hot filtration, the filter cake was rinsed once with 200mL toluene an...

Embodiment 3

[0050] Add 100g of terphenyl and 1L of bromobenzene into a 2L reaction flask, add 174g of liquid bromine under stirring, and then raise the temperature to 110°C for 40 hours to react. Using low temperature (-10-0°C) condensation, at least part of the Br produced by heating terphenyl and liquid bromine 2 The steam is condensed and refluxed to the reaction bottle, and at least part of the Br 2 and hydrogen bromide vapors are absorbed using water.

[0051] After cooling to 25°C, pour the reaction solution of terphenyl and liquid bromine into 2L of methanol, stir for 0.5 hour, filter, and wash the filter cake at least once with 800mL of methanol. After filtering, the filter cake was dried at 60° C. for 2 hours in a blast oven. The dried crude product was added to 200mL toluene for reflux and beating for 12 hours. After hot filtration, the filter cake was rinsed once with 200mL toluene and then sucked dry. Add the drained filter cake to 200 mL of toluene and reflux for beating f...

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Abstract

The invention relates to a method for synthesizing 4,4'-dibromo p-terphenyl. The method comprises the following steps: enabling terphenyl, liquid bromine and at least one organic solvent at 100 to 110DEG C; reacting for 24 to 48h in the absence of a catalyst, so as to obtain a first reaction mixture, wherein the mol ratio of terphenyl to liquid bromine is 1 to (2.25 to 2.75); cooling to 25 to 30DEG C; after washing with methanol, filtering to obtain a first crude product; purifying the first crude product to obtain the product 4,4'-dibromo p-terphenyl. The method provided by the invention has the beneficial effects that no catalyst is adopted and the yield still reaches 70 percent, so that the cost is reduced and a post-treatment flow is simplified; technical supports are provided for industrial production of the 4,4'-dibromo p-terphenyl.

Description

technical field [0001] This application relates to the technical field of organic synthesis. Specifically, the application relates to a method for synthesizing 4,4'-dibromo-p-terphenyl. Background technique [0002] P-terphenyl compounds have the advantages of good light, heat, electricity, and chemical stability, and adjustable physical constants such as anisotropy, viscosity, and birefringence. Compared with other liquid crystal building units connected by two or more benzene rings through esters, amides, azo groups, etc., it has more advantages, so it is widely used in liquid crystal terminal display devices (LCD) and preparation of light-emitting diodes ( LED) polymer blue light material. [0003] At present, 4,4'-dibromo-p-terphenyl is an important intermediate for the synthesis of p-terphenyl compounds, biphenyl liquid crystals and some organic electroluminescent materials. In the known synthetic method, for example, US Pat. No. 7,544,842B1 discloses that 4,4' -dib...

Claims

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Application Information

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IPC IPC(8): C07C17/12C07C25/18
CPCC07C17/12C07C25/18
Inventor 傅志伟贺宝元潘新刚余文卿陆伟郭有壹吴青
Owner XUZHOU B&C CHEM CO LTD
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