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Benzoate compound and synthesis method and application thereof

A technology of ester compounds and synthesis methods, which is applied in the field of pollution control of organic small molecule compounds, can solve the problems of inability to reduce the secondary pollution of heavy metal detection reagents and cannot be reused, achieve low synthesis and detection costs, and avoid secondary pollution , the effect of mild synthetic conditions

Active Publication Date: 2017-05-10
HUAIYIN TEACHERS COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The object of the present invention is to provide a kind of benzoic acid ester compound and its synthetic method and application, aim at solving existing benzoic acid ester compound can not be used for selective identification and monitoring heavy metal ion by choosing different substituents, cannot repeat Utilization, can not reduce the problem of secondary pollution of heavy metal detection reagents to the environment

Method used

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  • Benzoate compound and synthesis method and application thereof
  • Benzoate compound and synthesis method and application thereof
  • Benzoate compound and synthesis method and application thereof

Examples

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preparation example Construction

[0050] like figure 1 As shown, the synthetic method of the benzoate compound provided in the embodiment of the present invention comprises:

[0051] S101: add 4-(9-carbazolyl) benzoate to the reactor, add 20 mL to 60 mL of tetrahydrofuran, stir under cooling, add N-bromosuccinimide, and continue stirring overnight after the addition to obtain 4 -[(3-Bromo)-9-carbazolyl]benzoate;

[0052] S102: add 4-[(3-bromo)-9-carbazolyl]benzoate to the reactor, 0.1 g-1 g of anhydrous carbonate, 0.1-1 g of tetrakistriphenylphosphine palladium, 20-1 g of tetrahydrofuran 60mL; N 2 Heating and stirring under protection, adding 5-aldehyde-2-thiopheneboronic acid in the amount of 4-[(3-bromo)-9-carbazolyl]benzoate and other substances dropwise to the reaction solution, and reacting for 3h~ 5h; the product was separated by column chromatography to obtain 4-(3-(5'-formylthiophene)-9-carbazolyl)benzoate;

[0053] S103: add 4-(3-(5'-formylthiophene)-9-carbazolyl)benzoate to the reactor, dissolve ...

Embodiment 1

[0065] Example 1: Synthesis of methyl 4-[(3-bromo)-9-carbazolyl]benzoate

[0066] 4-(9-carbazolyl) benzoic acid methyl ester (2.41g, 4mmol) was added to a 100mL three-necked flask, solvent tetrahydrofuran 30mL, stirred at -30 ° C for 20min, a small amount of N-bromobutane was slowly added for several times Diimide (0.712 g, 4 mmol), stirring was continued for 15 min and at room temperature overnight. Rotary-evaporated, dissolved in chloroform, washed with deionized water (3×100 mL), rotary-evaporated, and recrystallized from absolute ethanol to obtain methyl 4-[(3-bromo)-9-carbazolyl]benzoate. 1 HNMR (400MHz, DMSO, δppm): 8.539 (s, 1H, Ar), 8.333 (d, 1H, Ar), 8.246 (d, 2H, Ar), 7.822 (d, 2H, Ar), 7.584 (d, 2H) ,Ar),7.462(m,3H,Ar),7.391(m,1H,Ar),3.931(s,3H,CH 3 ).

Embodiment 2

[0067] Example 2: Synthesis of .4-[(3-bromo)-9-carbazolyl]benzoic acid ethyl ester

[0068] Same as Example 1, wherein methyl 4-(9-carbazolyl)benzoate is replaced by ethyl 4-(9-carbazolyl)benzoate.

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Abstract

The invention discloses a benzoate compound and a synthesis method and application thereof. The benzoate compound refers to a 4-(3-(5'-((trans)-substituent imine)methyl)-2-thienyl)-9- carbazolyl)benzoate compound. The synthesis method and application include firstly, synthesizing a target product from 4-(9-carbazolyl)benzoate; secondly, establishing a method for fluorescent recognition and detection of heavy metal ions by the target product. The synthesis method has the advantages that the synthesis method is simple, mild in synthesis condition and high in yield; the target product is enhanced in fluorescence under the action of the heavy metal ions and can be used for selectively recognizing and monitoring different heavy metal ions by selecting different substituents, thereby being high in sensitivity; the target product is reusable and recyclable, so that secondary pollution to the environment due to heavy metal detection reagents is reduced.

Description

technical field [0001] The invention belongs to the technical field of pollution control and application of organic small molecular compounds, and in particular relates to a benzoate compound and a synthesis method and application thereof. Background technique [0002] With the vigorous development of modern industry and the rapid growth of the world population, serious environmental pollution problems have arisen. Among them, transition metals (such as Co 2+ , Hg 2+ , Pb 2+ , Cd 2+ , Cu 2+ etc.) pollution has become one of the most serious pollution. They mainly come from the combustion of fossil fuels, the discharge of waste liquid, waste water and waste from the metallurgical industry and chemical industry. Because transition metals cannot be decomposed by environmental microorganisms and are easily accumulated, they can be converted into more toxic compounds in the environment, changing soil properties and affecting river and air quality. Even some metals accumula...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D409/04C07D409/14C07D417/14C09K11/06G01N21/64
CPCC07D409/04C07D409/14C07D417/14C09K11/06C09K2211/1029C09K2211/1037C09K2211/1044C09K2211/1092G01N21/6428Y02P20/582
Inventor 张宇赵剑英魏旭辉马奎蓉胡化友蒋正静
Owner HUAIYIN TEACHERS COLLEGE
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