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Preparation method of alkyl cyclohexyl cyanobiphenyl liquid crystal compound

A technology based on liquid crystal compounds and biphenylnitrile, which is applied in chemical instruments and methods, liquid crystal materials, etc., and can solve problems such as high safety risks, environmental pollution, and unreasonable synthetic routes

Inactive Publication Date: 2017-07-21
YANTAI DERUN LIQUID CRYSTAL MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] This preparation process has the following problems: 1. The synthetic route is long and there are too many steps; the 9-step reaction is prepared from one end to the end step by step, and the comprehensive total yield is very low, which is uneconomical; the designed synthetic route is unreasonable; 2. Two-step hydrogenation reaction steps , the first step is high-pressure hydrogenation, which has high safety risks and is not conducive to industrial production; ③ many impurities are introduced, which makes purification difficult and the quality is not easy to guarantee; ④ expensive iodine and iodic acid are used, and the yield of iodination reaction is not high; ⑤ The cyanolysis reaction uses cuprous cyanide, which pollutes the environment and has great potential safety hazards, which is contrary to the current implementation of green and environmental protection production; therefore, many disadvantages cause poor product quality, high product cost, lack of competitiveness, and are not conducive to large-scale production

Method used

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  • Preparation method of alkyl cyclohexyl cyanobiphenyl liquid crystal compound
  • Preparation method of alkyl cyclohexyl cyanobiphenyl liquid crystal compound
  • Preparation method of alkyl cyclohexyl cyanobiphenyl liquid crystal compound

Examples

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Effect test

Embodiment 1

[0072] Taking the preparation of n-pentylcyclohexylbiphenylnitrile {trans-4-(4-n-pentylcyclohexyl)-[1,1-biphenyl]-4-carbonitrile)} liquid crystal compound (I-1) as an example , specify the preparation method of pentylcyclohexyl biphenyl nitrile liquid crystal compound:

[0073] Step a: Preparation of trans-4-(4-n-pentylcyclohexyl)phenylboronic acid (Ⅲ-1):

[0074] Install equipment and feed: Add 14L dry tetrahydrofuran to the reaction kettle, install the reaction kettle, nitrogen protection device (balloon), dropping device and cooling device, vent nitrogen for 3 to 4 times, maintain a slight positive pressure, and maintain It takes about 1 to 1.5 hours for the balloon to stand in a stable state, pass liquid nitrogen to cool down, control the cooling speed, and prevent the balloon from sucking back.

[0075] Cooling+dropping 1: When the temperature drops below -80°C, use a nitrogen pressure device to press 11mol of n-butyllithium into the dropping funnel at a stable speed, th...

Embodiment 2

[0104] Preparation of trans-4-(4-n-pentylcyclohexyl)phenylboronic acid (Ⅲ-1):

[0105] The preparation process is the same as in Example 1, except that the n-butyllithium in step a is replaced by sec-butyllithium, and the other steps are similar, and 2.49kg of white solid---HPLC≥99.0% of the target product (Ⅲ -1), yield: 91%.

Embodiment 3

[0107] Preparation of trans-4-(4-n-pentylcyclohexyl)phenylboronic acid (Ⅲ-1):

[0108] The preparation process is the same as in Example 1, except that the 2.76kg triisobutyl borate raw material in step a is replaced by 1.250kg trimethyl borate, and other steps are similar, and 2.44kg white solid is prepared---HPLC≥99.0% The target product (Ⅲ-1), yield: 89%.

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Abstract

The invention discloses a preparation method of an alkyl cyclohexyl cyanobiphenyl liquid crystal compound. The preparation method comprises the following steps: adopting trans-4-(4-alkyl cyclohexyl)bromobenzene to react with a metal organic lithium reagent and a boronizing reagent to prepare trans-4-(4-alkyl cyclohexyl)phenylboronic acid; then reacting with p-halogenating cyanophenyl; using a palladium compound as a main catalyst; adding a ligand and a catalyst promoter to form a good Suzuki coupling reaction system; and carrying out a Suzuki coupling reaction to prepare a target compound alkyl cyclohexyl cyanobiphenyl{trans-4-(4-alkyl cyclohexyl)-[1,1-biphenyl]-4-formonitrile)}. The adopted raw materials are easy to get, the synthetic steps are simplified, and a synthetic route innovates, so that the time cost is reduced, the efficiency is improved, the product cost is reduced, the quality is promoted, and the product market competitiveness is greatly promoted.

Description

technical field [0001] The present invention relates to a new preparation of alkylcyclohexylbiphenylnitrile {chemical name: trans-4-(4-alkylcyclohexyl)-[1,1-biphenyl]-4-carbonitrile} liquid crystal compound The method belongs to the technical field of preparation of liquid crystal compounds. Background technique [0002] Liquid crystal material is one of several key materials constituting a liquid crystal display (LCD), and with different display modes, the required liquid crystal materials are also different. In order to meet the corresponding characteristics required by various liquid crystal display devices, it is often necessary to mix and use more than 10 kinds of liquid crystal compounds with different properties to balance and optimize their performance, so as to meet the performance required by the display mode. [0003] Alkylcyclohexylbiphenylnitrile {chemical name: trans-4-(4-alkylcyclohexyl)-[1,1-biphenyl]-4-carbonitrile} liquid crystal compound because of its la...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K19/30
CPCC09K19/3003C09K2019/3016
Inventor 刘鑫勤孙伟姜东全李强于青春
Owner YANTAI DERUN LIQUID CRYSTAL MATERIALS
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