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3'-(4-bromonaphthalene-1-yl)[1,1'-biphenyl]-4-carbonitrile and its synthetic method

A technology of biphenyl and nitrile biphenyl, applied in the field of 3'-[1,1'-biphenyl]-4-nitrile and its synthesis, achieving the advantages of simple process synthesis method, improved stability and luminous performance Effect

Active Publication Date: 2020-06-05
HENAN ACADEMY OF SCI CHEM RES INST CO LTD
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Problems solved by technology

[0004] Aiming at the current status of organic electroluminescent materials, the object of the present invention is to provide an organic electroluminescent material 3'-(4-bromonaphthalene-1-yl)[1,1'-biphenyl]-4-carbonitrile and its resolve resolution

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  • 3'-(4-bromonaphthalene-1-yl)[1,1'-biphenyl]-4-carbonitrile and its synthetic method
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  • 3'-(4-bromonaphthalene-1-yl)[1,1'-biphenyl]-4-carbonitrile and its synthetic method

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Embodiment Construction

[0021] For a better description of the present invention, examples are as follows:

[0022] (1) Synthesis of 3-bromo-4'-cyanobiphenyl (a)

[0023] Under the protection of argon, add 364g of 4-bromobenzonitrile, 402g of 3-bromophenylboronic acid, 1596g of potassium phosphate trihydrate, 6g of tris(o-tolyl)phosphine, 2L of dioxane and 0.5L of water into a 5L three-necked flask successively , after the reaction system air was replaced by argon, the catalyst tris(dibenzylideneacetone)dipalladium (Pd 2 (dba) 3 ) 4.5g, control the reaction temperature at 55°C for 6h, HPLC detects that the reaction is over, add water to the reaction solution, extract with 2L dichloromethane, dry over anhydrous magnesium sulfate, recover the solvent under reduced pressure, and obtain a brown oil, which is obtained by rectification. Yellow liquid 3-bromo-4'-nitrile biphenyl 93.4g, content 99.2%, yield 96.5%, melting point: 33.6-34.5°C.

[0024] 1 H NMR (400MHz, CDCl 3 ), δ: 7.748-7.723 (3H, m), 7....

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Abstract

The invention discloses 3'-(4-bremnaphthalene-1-yl)[1,1'-xenyl]-4-nitrile and a synthetic method thereof and belongs to the field of organic synthesis. The synthetic method comprises the following steps: taking 4-bromobenzonitrile as a raw material, and sequentially carrying out a Suzuki coupled reaction and a Miyanra boronizing reaction to synthesize 3-boronic acid pinacol ester-4'-nitrile biphenyl; taking 3-boronic acid pinacol ester-4'-nitrile biphenyl and 1-bromo-4-iodonaphthalene as raw material, and synthesizing the target compound by virtue of the Suzuki coupled reaction. The syntheticmethod is simple, high in yield and applicable to industrialized production. The compound can serve as an important host-guest adulterant material in an organic electroluminescence material.

Description

technical field [0001] The present invention relates to 1,4-disubstituted naphthalene compound modified by biphenyl group and its synthesis method, in particular to 3'-(4-bromonaphthalene-1-yl)[1,1'-biphenyl]-4- Nitrile and its synthesis method belong to the field of organic synthesis. Background technique [0002] Biphenyl is an important class of organic chemical raw materials, widely used in medicine, pesticides, dyes, liquid crystal materials and other fields. It can be used in the synthesis of plasticizers and preservatives, as well as in the manufacture of fuels, engineering plastics and high-energy fuels. Studies have shown that the conjugated π-electrons in nitrile-containing biphenyl derivatives can endow it with excellent photoelectric performance, making it have good hole transport ability and high luminescence ability. The bulky aromatic groups of nitrile-containing biphenyl derivatives can inhibit the close packing of molecules and the formation of complexes, ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C253/30C07C255/50C09K11/06
CPCC07C253/30C07C255/50C07F5/04C09K11/06C09K2211/1007C09K2211/1011
Inventor 杨振强屈凤波曹继红马欣周铎陈鹏丽杨瑞娜
Owner HENAN ACADEMY OF SCI CHEM RES INST CO LTD
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