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New synthetic method of 4-halogenated phenylacetylene

A technology of halogenated benzene and a new method, which is applied in the field of synthesis of halogenated phenylacetylenes, can solve the problems of low yield of target products, difficult purification of products, and great environmental hazards, and achieve high product purity, easy control, and high yield reasonable effect

Inactive Publication Date: 2015-01-07
NANJING XIAOZHUANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] There are following problems and shortcomings in the above synthetic method: the solvent used in the first synthetic method is mostly a toxic solvent that is harmful to the environment, and the product is not easy to purify
In the second synthetic method using PCl 5 Extremely inconvenient, acetophenones are controlled drugs, difficult to purchase, and the yield of the target product is not high

Method used

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  • New synthetic method of 4-halogenated phenylacetylene
  • New synthetic method of 4-halogenated phenylacetylene
  • New synthetic method of 4-halogenated phenylacetylene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062]

[0063] In the first step, dissolve 4-bromobenzaldehyde in 4 equivalents of acetic anhydride, add 1.5 equivalents of anhydrous potassium carbonate, control the temperature at 130-140 degrees, monitor by TLC until the conversion of the substrate is complete, and isolate product 1;

[0064] In the second step, the product 1 was dissolved in an appropriate amount of glacial acetic acid, and 1.5 equivalents of liquid bromine was added dropwise thereto under the condition of 60 degrees, and the product 2 was isolated by TLC monitoring until the conversion of the substrate was complete;

[0065] In the third step, the product 2 was dissolved in an appropriate amount of acetone, and 3 equivalents of sodium bicarbonate was added thereto under the condition of 55-60 degrees, and the product 3 was isolated by TLC monitoring until the conversion of the substrate was complete;

[0066] In the fourth step, the product 3 was dissolved in an appropriate amount of ethanol, and 3 equ...

Embodiment 2

[0068]

[0069] In the first step, dissolve 4-bromobenzaldehyde in 4 equivalents of acetic anhydride, add 1.5 equivalents of anhydrous sodium carbonate, control the temperature at 130-140 degrees, monitor by TLC until the conversion of the substrate is complete, and isolate product 1;

[0070] In the second step, the product 1 was dissolved in an appropriate amount of glacial acetic acid, and 1.5 equivalents of liquid bromine was added dropwise thereto under the condition of 60 degrees, and the product 2 was isolated by TLC monitoring until the conversion of the substrate was complete;

[0071] In the third step, the product 2 was dissolved in an appropriate amount of acetone, and 3 equivalents of sodium bicarbonate was added thereto under the condition of 55-60 degrees, and the product 3 was isolated by TLC monitoring until the conversion of the substrate was complete;

[0072] In the fourth step, the product 3 was dissolved in an appropriate amount of ethanol, and 3 equiva...

Embodiment 3

[0074]

[0075] In the first step, dissolve 4-bromobenzaldehyde in 4 equivalents of acetic anhydride, add 1.5 equivalents of anhydrous sodium bicarbonate, control the temperature at 130-140 degrees, monitor by TLC until the conversion of the substrate is complete, and isolate product 1;

[0076] In the second step, the product 1 was dissolved in an appropriate amount of glacial acetic acid, and 1.5 equivalents of liquid bromine was added dropwise thereto under the condition of 60 degrees, and the product 2 was isolated by TLC monitoring until the conversion of the substrate was complete;

[0077] In the third step, the product 2 was dissolved in an appropriate amount of acetone, and 3 equivalents of sodium bicarbonate was added thereto under the condition of 55-60 degrees, and the product 3 was isolated by TLC monitoring until the conversion of the substrate was complete;

[0078] In the fourth step, the product 3 was dissolved in an appropriate amount of ethanol, and 3 equi...

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Abstract

The invention discloses a new synthetic method of 4-halogenated phenylacetylene, which comprises the following steps: taking 4-halogenated benzaldehyde and acetic anhydride which are cheap and are easy to obtain as raw materials and obtaining the 4-halogenated benzaldehyde which is a final target product through Perkin reaction, bromination reaction and debromination, decarboxylation and elimination reaction. The new synthetic method has the benefits that as the 4-halogenated benzaldehyde and the acetic anhydride are taken as substrates, and an environmental protection solvent with low toxicity is adopted in the reaction process, the new synthetic method has the characteristics of greenness and environmental protection, high efficiency, low cost, reasonable yield, mild reaction conditions and easiness in control; through the optimization of the reaction conditions and a post-processing method, in particular to an innovative application of a sublimation method to product purification, the new synthetic method disclosed by the invention also has the characteristic of high product purity.

Description

technical field [0001] The invention relates to a new method for synthesizing 4-halogenated phenylacetylenes, belonging to the technical field of synthesis of halogenated phenylacetylenes. Background technique [0002] Halogenated phenylacetylene is an important class of electronic chemical raw materials and organic synthesis intermediates. It is widely used in medicines, pesticides, catalysis, liquid crystal intermediates, polymerization inhibitors, electrode materials, luminescent coatings, corrosion inhibitors, etc. At present, the commonly used methods for synthesizing halogenated phenylacetylenes include the synthesis method from substituted acetophenone, substituted styrene, heterocyclic compound, etc., and the synthesis method through Vilsmerier reaction. [0003] In the prior art, there are two main technical routes for synthesizing 4-halogenated phenylacetylenes: [0004] The first: [0005] [0006] The second: [0007] [0008] The above synthetic method...

Claims

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Application Information

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IPC IPC(8): C07C25/24C07C17/25C07C17/363C07C57/58C07C51/363C07C51/083
Inventor 喻敏刘光祥周宏薛蒙伟李健
Owner NANJING XIAOZHUANG UNIV
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