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Aryl halide derivatives and synthesis method thereof

A synthesis method and derivative technology, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of few reports of aromatic halogen compounds, achieve high yield and broad application prospects

Active Publication Date: 2014-09-03
ANHUI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this reaction is limited to the introduction of fluorine atoms, and there are very few reports on the preparation of aromatic halides by Domino cyclization.

Method used

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  • Aryl halide derivatives and synthesis method thereof
  • Aryl halide derivatives and synthesis method thereof
  • Aryl halide derivatives and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Synthesis of Aryl Halide Derivatives:

[0047] The synthetic route is shown below.

[0048]

[0049] a. Precursor synthesis:

[0050] The precursor synthesis was prepared by a Cadiot-Chodkiewicz coupling reaction. Weigh 4-methyl-N, N-dipropargylbenzenesulfonamide (4.94g, 20mmol), CuCl (3.48g, 40mmol), NH 2 OH·HCl (0.28g, 4mmol) was placed in a 250mL round-bottomed flask, and in an ice-water bath, 60mL of 30% n-butylamine solution was added dropwise, stirred for 10 minutes after the addition, and then added dropwise such as 1-bromo-1 - Hexyne (9.60g60mmol), after addition, react for 4 hours; after reaction, wash with water, extract with ethyl acetate, and dry over anhydrous magnesium sulfate. The solvent was evaporated and separated by silica gel column chromatography (eluent: petroleum ether / ethyl acetate 20:1) to obtain compound 1.

[0051] b. Tandem cyclization reaction:

[0052] Weigh compound 1 (407mg, 1mmol), put it in a 10mL straight tube, add a mixed soluti...

Embodiment 2

[0062] Synthesis of Aryl Halide Derivatives:

[0063] The synthetic route is shown below.

[0064]

[0065] a. Precursor synthesis:

[0066] The precursor synthesis was prepared by a Cadiot-Chodkiewicz coupling reaction. Weigh respectively diyne compound (4.12g, 20mmol), CuCl (3.48g, 40mmol), NH 2 OH·HCl (0.28g, 4mmol) was placed in a 250mL round-bottomed flask, and in an ice-water bath, 60mL of 30% n-butylamine solution was added dropwise, stirred for 10 minutes after the addition, and then added dropwise such as 1-bromo-1 - Hexyne (12.60g, 60mmol), after addition, react for 4 hours; after reaction, wash with water, extract with ethyl acetate, and dry over anhydrous magnesium sulfate. The solvent was evaporated and separated by silica gel column chromatography (eluent: petroleum ether / ethyl acetate 20:1) to obtain compound 3.

[0067] b. Tandem cyclization reaction:

[0068] Weigh compound 3 (466mg, 1mmol), place it in a 10mL straight tube, add a mixed solution of 5mL...

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Abstract

The invention relates to aryl halide derivatives and a synthesis method thereof. The structural formula of the aryl halide derivatives is disclosed in the specification. The synthesis method comprises the following steps: precursor synthesis, cyclic addition and purification. The condensed ring aryl halide derivatives can be used as a drug intermediate or drug, or an important intermediate in organic synthesis, and has wide application prospects in the field of organic synthesis.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to an aromatic halide derivative and a synthesis method thereof. Background technique [0002] Arylhalogen compounds refer to compounds with one or more halogen atoms attached to the aromatic ring, and the common ones are halogenated benzene compounds. Due to the p-Π conjugation effect between the halogen atom and the aromatic ring in the aromatic halide compound, the reactivity of the carbon-halogen bond is not high, but under certain conditions, some reactions can also occur, and some reactions have practical value or theoretical significance. One of the industrial production methods of phenol is obtained by acidification and hydrolysis of chlorobenzene and strong alkali under high temperature and pressure. For a period of time, chlorobenzene has been widely used in the production of DDT (DDT) pesticides. The reaction of chlorobenzene and sodium phenate is ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/44C07C69/757C07C67/307
CPCC07C67/307C07C69/757C07C2602/08C07D209/44
Inventor 李立冬胡益民吴玉芹
Owner ANHUI NORMAL UNIV
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