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Method for synthesizing unsaturated ring halide

An unsaturated and halide technology, applied in the field of synthesizing unsaturated ring halide, can solve the problem of high preparation cost, and achieve the effect of reducing preparation cost, high yield and good selectivity

Pending Publication Date: 2022-06-28
ASYMCHEM LAB TIANJIN
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The main purpose of the present invention is to provide a method for synthesizing unsaturated ring halides, to solve the problem of high preparation cost of halides with unsaturated ring structures in the prior art

Method used

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  • Method for synthesizing unsaturated ring halide

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Experimental program
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Effect test

Embodiment 1

[0037] Preparation of methyl 4-bromo-1-methylpyrazole-3-carboxylate

[0038] Magnons were added to a non-membrane electrolytic cell (10 mL) at room temperature of 25 °C, followed by the substrate 1-methylpyrazole-3-carboxylate methyl ester (70.1 mg, 0.5 mmol) and bromide to the cell. Sodium (77.3 mg, 0.75 mmol, 1.5 eq.). Acetonitrile (4 mL) and purified water (1 mL) were added using a syringe, followed by acetic acid (60.0 mg, 1 mmol, 2 eq.) using a microsyringe. After all the materials were added, the pH value of the reaction solution was 4, and the cathode and anode were equipped with graphite sheets (1×7×0.3cm 3 ), the electrode immersion area (that is, the area immersed in water and opposite to the other pole, the same in the following embodiments) is 1 cm 2 . The reaction solution was stirred and mixed, and 6 F was electrolyzed under a constant current of 100 mA. After the reaction, water and ethyl acetate were added for extraction and separation. The organic phase wa...

Embodiment 2

[0041] Preparation of 3-bromoindole

[0042] A non-membrane electrolytic cell (10 mL) was charged with magneton at room temperature of 25°C, followed by substrate indole (59.2 mg, 0.5 mmol), sodium bromide (77.3 mg, 0.75 mmol, 1.5 eq. ). Acetonitrile (4 mL) and purified water (1 mL) were added using a syringe. After all the materials were added, the pH value of the reaction solution was 7, and the cathode and anode were equipped with graphite sheets (1×7×0.3 cm 3 ), the electrode immersion area is 1 cm 2 . The reaction solution was stirred and mixed, and 4 F was electrolyzed under a constant current of 100 mA. After the reaction, water and ethyl acetate were added for extraction and separation. The organic phase was dried with anhydrous sodium sulfate and then concentrated. The target product was obtained by column chromatography, and the isolated yield was 90.7%. The reaction equation is as follows:

[0043] Formula (2)

Embodiment 3

[0045] Preparation of methyl 3-bromoindole-5-carboxylate

[0046] A non-membrane electrolytic cell (10 mL) was charged with magnons at room temperature of 25°C, followed by the substrate indole-5-carboxylate methyl ester (87.6 mg, 0.5 mmol), sodium bromide (77.3 mg) to the cell. , 0.75 mmol, 1.5 eq.). Add acetonitrile (4 mL) and purified water (1 mL) using a syringe. After all the materials were added, the pH value of the reaction solution was 7, and the cathode and anode were equipped with graphite sheets (1×7×0.3 cm 3 ), the electrode immersion area is 1 cm 2 . The reaction solution was stirred and mixed, and 4 F was electrolyzed under a constant current of 100 mA. After the reaction, water and ethyl acetate were added for extraction and separation. The organic phase was dried with anhydrous sodium sulfate and then concentrated. The target product was obtained by column chromatography, and the isolated yield was 87.1%. The reaction equation is as follows:

[0047] Fo...

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Abstract

The invention provides a method for synthesizing an unsaturated ring halide. The method comprises the following steps: mixing a substrate, a halide and a solvent to form a reaction solution, and under the condition that constant current is applied in a diaphragm-free electrolytic cell, reacting by taking electrons as an oxidation-reduction reagent to synthesize a corresponding halide of which hydrogen on an unsaturated ring is substituted, the substrate comprises any one or more of pyrazole, indole, indazole, pyrrole, thiophene, furan, naphthalene, aryl ether and arylamine. According to the scheme, a halogen active intermediate is generated on line by using an anodic oxidation strategy, so that not only can a monohalide be synthesized, but also preparation of polyhalogenated unsaturated ring compounds such as dihalogen substitution and trihalogen substitution can be realized. The halide is wide in source, low in price and easy to obtain, the method for synthesizing the unsaturated cyclic halide is convenient to implement, the preparation cost of the unsaturated cyclic compound halide can be effectively reduced, and generation of extra waste is reduced.

Description

technical field [0001] The present invention relates to a method for synthesizing halogen-substituted compounds, in particular, to a method for synthesizing unsaturated ring halides. Background technique [0002] Unsaturated ring halides are important chemical raw materials and pharmaceutical intermediates, which are widely used in the synthesis of various natural products and drug molecules. Halogen functional groups can be effectively converted into other functional groups through nucleophilic substitution, nucleophilic addition, reductive hydrogenation, and transition metal-catalyzed coupling reactions, so as to realize the synthesis of various functional molecules; therefore, unsaturated ring halides are especially halogenated. Substituted aromatic hydrocarbons are important precursors for the synthesis of many complex organic molecules, and how to synthesize various unsaturated ring halides in a green and efficient manner is also a goal that people have been exploring. ...

Claims

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Application Information

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IPC IPC(8): C25B3/11C25B3/09C25B3/07C25B3/05C25B3/23C25B3/27C25B9/17
CPCC25B3/11C25B3/09C25B3/07C25B3/05C25B3/23C25B3/27C25B9/17
Inventor 洪浩王攀汤平平詹姆斯·盖吉肖毅高新隆
Owner ASYMCHEM LAB TIANJIN
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