2-R-4'-bromomethyl biphenyl and preparation method thereof

A technology of bromomethyl biphenyl and methyl biphenyl, which is applied in the field of 2-R-4'-bromomethyl biphenyl and its synthesis, and can solve the problems of unsuitability for industrialized production, low bromine atom economy, and bromine source activity. Low cost, low requirements and high reactivity

Active Publication Date: 2015-07-01
阜阳欣奕华制药科技有限公司 +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The invention provides a method for preparing 2-R-4'-bromomethylbiphenyl, which is used to solve the problem of low bromine source activ

Method used

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  • 2-R-4'-bromomethyl biphenyl and preparation method thereof
  • 2-R-4'-bromomethyl biphenyl and preparation method thereof
  • 2-R-4'-bromomethyl biphenyl and preparation method thereof

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Embodiment approach

[0034] According to one embodiment of the present invention, the third organic solvent is selected from one of the following: acetonitrile, dichloromethane, 1,2-dichloroethane, chlorobenzene and ethyl acetate, more preferably di Chloromethane, ethyl acetate and acetonitrile.

[0035] The solvent in the method selects water and the first organic solvent as the mixed solvent, so the first organic solvent adopts a solvent with better compatibility with water, and the reaction effect will be better. In addition, according to the second organic solvent of the method of the present invention, organic solvents such as ethyl acetate, dichloromethane and acetonitrile can be selected according to the extraction effect.

[0036] 2-R-4'-bromomethylbiphenyl obtained according to the preparation method of the present invention, wherein the R group is selected from one of the following: -CN, -COO-, -CONH 2 -, -F, -Cl, -Br and -I.

[0037] The 2-R-4'-bromomethylbiphenyl according to the prese...

Embodiment 1

[0040] According to the preparation method of 2-R-4'-bromomethylbiphenyl shown in the present invention, wherein R is -CN, the method provides raw materials: 2-cyano-4'-methylbiphenyl, sodium bromate, Sodium bromide, concentrated sulfuric acid, water and the first organic solvent; wherein, the molar ratio of sodium bromate and 2-cyano-4'-methylbiphenyl is 0.1:1; sodium bromide and 2-cyano-4 The molar ratio of '-methylbiphenyl is 0.5:1; the molar ratio of concentrated sulfuric acid to 2-cyano-4'-methylbiphenyl is 0.25:1; the first organic solvent and 2-cyano-4'- The volume-to-weight ratio of methylbiphenyl is 4:1ml / g; the volume-to-weight ratio of water as a solvent to 2-cyano-4'-methylbiphenyl is 5:1ml / g; the water used to dilute concentrated sulfuric acid The volume-to-weight ratio to concentrated sulfuric acid is 5:1ml / g, and the first organic solvent is dichloromethane. The specific amount of raw materials added is as follows: 2-cyano-4'-methylbiphenyl 100g (517.5mmol, 1eq...

Embodiment 2

[0045] According to the preparation method of 2-R-4'-bromomethylbiphenyl shown in the present invention, wherein the R group is -CN, the method provides raw materials: 2-cyano-4'-methylbiphenyl, sodium bromate , sodium bromide, concentrated sulfuric acid, water and the first organic solvent; wherein, the molar ratio of sodium bromate to 2-cyano-4'-methylbiphenyl is 0.6:1; sodium bromide to 2-cyano- The mol ratio of 4'-methylbiphenyl is 1.2:1; the mol ratio of the concentrated sulfuric acid and 2-cyano-4'-methylbiphenyl is 1.2:1; the first organic solvent and 2-cyano- The volume-to-weight ratio of 4'-methylbiphenyl is 10:1ml / g; the volume-to-weight ratio of water and 2-cyano-4'-methylbiphenyl as solvent is 10:1ml / g; The volume-to-weight ratio of sulfuric acid water to concentrated sulfuric acid is 10:1ml / g, and the first organic solvent is acetonitrile. The specific amount of raw materials added is as follows: 100g (517.5mmol, 1eq) of 2-cyano-4'-methylbiphenyl, 46.8g (310.5mmo...

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Abstract

The invention discloses 2-R-4'-bromomethyl biphenyl and a preparation method thereof. According to the method provided by the invention, raw materials such as 2-R-4'-methyl biphenyl, sodium bromate, sodium bromide, concentrated sulfuric acid, water and a first organic solvent are provided. The method comprises the operation of a bromination step, namely 2-R-4'-methyl biphenyl, sodium bromate, sodium bromide and the water serving as a solvent are added in a reactor and are mixed uniformly, concentrated sulfuric acid diluted with water is added dropwise in the stirring reactor at 0-50 DEG C, and the reaction system keeps reacting for 4-12 hours at 0-50 DEG C to obtain a bromination product reaction liquid. According to the preparation method provided by the invention, the required raw materials are easily available, a bromine resource is generated during the reaction process and has high reactivity, the atom economy of bromine atoms is very high, the cost is low, the process condition is stable, the operation is simple, and requirements on a reaction kettle and corollary equipment are low, so that industrialization is easy to realize.

Description

technical field [0001] The invention relates to benzyl bromide compounds and a synthesis method thereof, in particular to 2-R-4'-bromomethyl biphenyl and a synthesis method thereof. Background technique [0002] Benzyl bromide compounds are important intermediates in organic synthesis, and 2-R-4'-bromomethylbiphenyl is an important intermediate in the preparation of sartan antihypertensive drugs. At present, 2-R-4'-methylbiphenyl is usually brominated to synthesize 2-R-4'-bromomethyl by using elemental bromine, elemental bromine / oxidant, bromosuccinimide and dibromohydantoin Biphenyl, the specific synthetic route is as figure 1 shown. [0003] But the above-mentioned method has the following problems: utilize elemental bromine to carry out bromination reaction, the amount of elemental bromine is generally 1.5 equivalents of the reaction substrate, and the consumption is more, and elemental bromine is a corrosive substance, and transportation and preservation are all very d...

Claims

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Application Information

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IPC IPC(8): C07C255/50C07C253/30C07C69/76C07C67/307
Inventor 孙睿尹强
Owner 阜阳欣奕华制药科技有限公司
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