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A kind of preparation method of o-iodobenzonitrile

A technology of benzonitrile and o-iodine, which is applied in the field of preparation of o-iodobenzonitrile, can solve the problems of easy production of by-products, polluting reagents that do not conform to the concept of green environmental protection, etc., and achieve high selectivity, low cost, and efficient reaction Effect

Inactive Publication Date: 2016-06-22
JIANGXI NORMAL UNIV
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

[0004] The purpose of the present invention is to provide a preparation method of o-iodobenzonitrile, aiming to solve the problem that the existing preparation method of o-iodobenzonitrile is easy to produce by-products, or the use of polluting reagents does not conform to the concept of green environmental protection

Method used

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  • A kind of preparation method of o-iodobenzonitrile
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preparation example Construction

[0017] The embodiment of the present invention provides a kind of preparation method of o-iodobenzonitrile, comprising the following steps:

[0018] S01. provide respectively the compound o-diphenyl iodide represented by following structural formula I and the compound malononitrile represented by structural formula II,

[0019]

[0020] S02. The o-diphenyl iodide and the malononitrile are heated and reacted in a catalyst and a ligand in a reaction solvent to generate a compound o-iodobenzonitrile represented by the following structural formula III,

[0021]

[0022] The reaction formula is expressed as:

[0023]

[0024] Wherein, the catalyst is cuprous bromide, the ligand is L-piperidine-2-carboxylic acid, the reaction solvent is dimethyl sulfoxide, the reaction temperature of the heating reaction is 90°C, and the reaction time is 12 hours.

[0025] Specifically, in the above step S01, the selection of the compound o-diphenyl iodide represented by structural formul...

Embodiment 1

[0036] A preparation method for o-iodobenzonitrile, comprising the following steps:

[0037] S01. Provide the compound o-diphenyliodide and the compound malononitrile respectively;

[0038] S02. In a 25mL round bottom flask, add 0.5mmol o-diiodobenzene and 0.5mmol malononitrile, then add 0.05mmol cuprous bromide, 0.1mmol L-2-pipercolic acid and 2mL dimethyl sulfoxide successively, The reaction was stirred at 90 °C for 12 hours, the reaction formula is as follows:

[0039]

Embodiment 2

[0041] A kind of preparation method of o-iodobenzonitrile also comprises the following steps on the basis of embodiment 1:

[0042] After cooling to room temperature, 10 mL of water was added to the system, and then extracted with 3×10 mL of ethyl acetate, dried over anhydrous sodium sulfate and evaporated to remove the solvent. The yield of pure o-iodobenzonitrile was obtained by silica gel column chromatography with a yield of 65%.

[0043] The o-iodobenzonitrile that obtains is carried out nuclear magnetic resonance test, and the test result of proton nuclear magnetic resonance spectrum and carbon spectrum is respectively as follows figure 1 , figure 2 It was determined by comparing it with the results reported in the literature.

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Abstract

The invention is applicable to the field of organic chemstry, and provides a preparation method of o-iodobenzonitrile. The preparation method comprises the following steps: respectively providing chemical compounds o-benzene diiodide and propanedinitrile; and performing a heating reaction in a reaction solvent including a catalyst and a ligan on the o-benzene diiodide and the propanedinitrile to generate the chemical compound o-iodobenzonitrile, wherein the catalyst is cuprous bromide, the ligand is L-piperidine-2-formic acid, the reaction solvent is dimethyl sulfoxide, the reaction temperature of the heating reaction is 90 DEG C, and the reaction time is 12 hours. The preparation method of o-iodobenzonitrile provided by the invention takes envrionmentally-friendly propanedinitrile as a cyanogen source, realizes the synthesis of the o-iodobenzonitrile through the selective cyanidation of o-diiodobiphenyl, is high in selectivity, can reach 65% in yield, meets the principle of envrionmental protection, is simple and convenient in operation and low in cost, and is suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of organic chemistry, in particular to a preparation method of o-iodobenzonitrile. Background technique [0002] Cyano and aryl carbon-iodine moieties are important organic functional groups in the field of organic chemistry and play a vital role in organic synthesis. Since o-iodobenzonitrile compounds contain both cyano and aryl carbon-iodine bonds, and the two are in the ortho position of the benzene ring, o-iodobenzonitrile can have excellent reactivity when used as an intermediate. Therefore, it is possible to design cascade reactions to synthesize organic compounds with diverse structures by utilizing the diverse reactivity of o-iodobenzonitrile. In view of the wide application of o-iodobenzonitrile compounds in organic synthesis, the synthesis of o-iodobenzonitrile compounds has become an important research content of organic synthetic chemistry. [0003] The traditional synthesis method is mainly through the ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C255/50C07C253/30
Inventor 万结平刘云云张毅
Owner JIANGXI NORMAL UNIV