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Method for synthesizing 4,6-bis(trichloromethyl)-2-p-acetyl biphenyl-1,3,5-triazine

A bis-trichloromethyl and acetyl biphenyl technology, applied in the direction of organic chemistry, can solve the problems of harsh reaction conditions, environmental pollution, cumbersome post-treatment, etc., and achieve the effect of mild reaction conditions, good yield and simple operation

Inactive Publication Date: 2009-05-27
HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There are many ways to oxidize hydrocarbon groups to carbonyl groups, such as the reported Cr(VI) or KMnO 4 , NaBiO 3 / AcOH, RuCl 2 (PPh 3 ) 3 -t -BuOOH,NaIO 4 / LiBr / H + These methods have disadvantages such as cumbersome post-processing, harsh reaction conditions, and pollution to the environment.

Method used

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  • Method for synthesizing 4,6-bis(trichloromethyl)-2-p-acetyl biphenyl-1,3,5-triazine
  • Method for synthesizing 4,6-bis(trichloromethyl)-2-p-acetyl biphenyl-1,3,5-triazine
  • Method for synthesizing 4,6-bis(trichloromethyl)-2-p-acetyl biphenyl-1,3,5-triazine

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Experimental program
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Effect test

Embodiment 1

[0020] A method for synthesizing 4,6-bistrichloromethyl-2-p-acetylbiphenyl-1,3,5-triazine, carried out according to the following steps:

[0021] a 1 .4,6-bistrichloromethyl-2-p-ethylbiphenyl-1,3,5-triazine preparation: add 0.02mol of p-ethylbiphenonitrile and 0.05mol of trichloroacetonitrile into the four-necked flask, Add 0.004mol of anhydrous aluminum trichloride, add 20.00mL of 1,2-dichloroethane as a solvent, stir, cool down the ice bath to 0°C, pass in dry HCl gas, remove the ice bath after 5h, and stir at room temperature for 20h. Excess trichloroacetonitrile and 1,2-dichloroethane were distilled off under reduced pressure, and the residue B was subjected to column chromatography to obtain 4.31 g of white solid A, namely 0.009 mol of 4,6-bistrichloromethyl-2-para Ethylbiphenyl-1,3,5-triazine, yield 44.00%.

[0022] 1 H-NMR (CDCl 3 , 500MHz):

[0023] 1.299 (t, 3H, CH 3 ), 2.726 (q, 2H, CH 2 ), 7.352(d, 2H, 4 CH), 7.635(d, 2H, 3 CH), 7.812(d, 2H, 2 CH), 8.751(d...

Embodiment 2

[0028] A method for synthesizing 4,6-bistrichloromethyl-2-p-acetylbiphenyl-1,3,5-triazine, carried out according to the following steps:

[0029] a 2 .4,6-bistrichloromethyl-2-p-ethylbiphenyl-1,3,5-triazine preparation:

[0030] Add 0.02mol of p-ethylbiphenylnitrile as raw material, 0.05mol of trichloroacetonitrile, 0.004mol of anhydrous aluminum trichloride, and 20.00mL of solvent 1,2-dichloroethane into a four-neck flask, stir, and drop the ice bath to 0 ℃, continue to feed dry HCl gas, remove the ice bath after 5h, and stir at room temperature for 24h. Excess trichloroacetonitrile and 1,2-dichloroethane were distilled off under reduced pressure, and the residue was subjected to column chromatography to obtain 4.31 g of white solid A, namely 0.009 mol of 4,6-bistrichloromethyl-2-p-ethane Biphenyl-1,3,5-triazine.

[0031] b 2 .4,6-bistrichloromethyl-2-p-acetylbiphenyl-1,3,5-triazine preparation: the obtained 4.31g white solid A and solvent dichloromethane 22.00mL, 30% H ...

Embodiment 3

[0033] A method for synthesizing 4,6-bistrichloromethyl-2-p-acetylbiphenyl-1,3,5-triazine, carried out according to the following steps:

[0034] a 3.4,6-bistrichloromethyl-2-p-ethylbiphenyl-1,3,5-triazine preparation: add 0.39mol of p-ethylbiphenonitrile and 0.97mol of trichloroacetonitrile into the four-necked flask, Add 0.078 mol of anhydrous aluminum trichloride, add 386.00 mL of 1,2-dichloroethane as a solvent, stir, cool down the ice bath to 0°C, pass in dry HCl gas, remove the ice bath after 20 h, and stir at room temperature for 18 h. Excessive trichloroacetonitrile and 1,2-dichloroethane were distilled off under reduced pressure, and the residue B was recrystallized from methanol and dichloromethane to obtain a white solid A with a weight of g 1 =49.40g; the crystallization mother liquor was placed at 0°C for 24h, and the weight was obtained in g 2 =38.10 g white solid A, yield 45.93%.

[0035] This step receives the total weight g=g of white solid A that is 4,6-bi...

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Abstract

The invention discloses a method for preparing a 1, 3, 5-triazine derivative with potential application in the fields such as photo-acid generators, insecticides, medicines, liquid crystal materials and so on, namely a method for synthesizing 4, 6-bistrichloromethyl-2-p-acetylbiphenyl-1, 3, 5-triazine, which comprises the following steps: a liquid crystal intermediate, namely p-ethyl cyanophenyl is taken as a raw material to prepare to obtain an intermediate product 4, 6-bistrichloromethyl-2-p-ethylbiphenyl-1, 3, 5-triazine, and then a target product is obtained through the oxidation. The synthesis method has the characteristics of mild reaction conditions, simple operation, small environmental pollution, safety and validity, and the obtained product can be used for preparing the photo-acid generators, the insecticides, the medicines, the liquid crystal materials and so on.

Description

technical field [0001] The invention relates to a preparation method of 1,3,5-triazine derivatives with potential applications in the fields of photoacid generators, insecticides, medicines, liquid crystal materials, etc., specifically a method for synthesizing 4,6- Trichloromethyl-2-p-acetylbiphenyl-1,3,5-triazine method. Background technique [0002] The photo-acid generator system produces photo-controlled acid under appropriate light conditions, which can lead to the decomposition or cross-linking reaction of acid-sensitive substances, so that the dissolution contrast between the illuminated part and the non-illuminated part increases, and image development is realized. Because the photoacid generator system has a good chemical amplification effect, high imaging sensitivity and recording accuracy, it is widely used in imaging systems. 1,3,5-Triazine derivatives are an important class of photoacid generators, and they are also intermediates of insecticides, drugs, liquid...

Claims

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Application Information

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IPC IPC(8): C07D251/24
Inventor 张越张艳艳李伟岭许苗云王春芳
Owner HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY
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