Preparation method of coronene

A coupling reaction and equivalent technology, which is applied in the preparation of organic compounds, chemical instruments and methods, and the production of hydrocarbons from oxygen-containing organic compounds, etc., can solve the problems of cumbersome operations, harsh conditions, and expensive raw materials, and achieve simple processes and efficient reactions. The effect of mild conditions and easy access to raw materials

Active Publication Date: 2016-07-27
江苏佳麦化工有限公司
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Problems solved by technology

[0013] The invention provides a preparation method of coronene, which solves the technical problems of expensive raw materials, harsh conditions, cumbersome operation and low yield in the prior art

Method used

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  • Preparation method of coronene
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preparation example Construction

[0031] According to the preparation method of coronene of the present invention, the method comprises:

[0032] Substitution reaction: use 1 equivalent of the compound shown in formula I and 4.2 to 5.6 equivalents of the compound shown in formula II in the presence of catalysts and auxiliary agents to carry out a coupling reaction in a solvent to convert it into a compound shown in formula III;

[0033] Ring-closing reaction: the compound shown in formula III undergoes ring-closing reaction in the presence of acid, and is converted into coronene shown in formula IV;

[0034]

[0035] The Chinese alias of corona benzene is Kou, and its molecular formula is C 24 h 12 , also known as hexabenzocene, is a polycyclic aromatic hydrocarbon with a highly symmetrical structure composed of six benzene rings fused around it; coronene exhibits blue-purple fluorescence in organic solvents.

[0036] In the preparation method of coronene of the present invention, the preparation method a...

Embodiment approach

[0043] According to one embodiment of the present invention, the amount of methanesulfonic acid or trifluoromethanesulfonic acid is 5-18 equivalents.

[0044] According to the preparation method of coronene of the present invention, when the amount of methanesulfonic acid or trifluoromethanesulfonic acid adopts the above-mentioned amount, the amount of by-products produced by the reaction will be reduced to the minimum, the purity of the product will be increased, and the product yield will be improved.

[0045] According to one embodiment of the present invention, the ring-closing step is reacted in dichloromethane solvent.

[0046] According to the preparation method of coronene of the present invention, in the substitution reaction, because the solubility of the compound shown in the formula III is good in methylene chloride, the compound shown in the formula III can be fully reacted and the product yield can be improved.

[0047] According to one embodiment of the present ...

Embodiment 1

[0054] The synthetic route is as follows:

[0055]

[0056] According to the preparation method of coronene of the present invention, first enter coupling reaction, under the protection of nitrogen, 5.2g (0.01mol, 1eq) compound shown in formula I (prepared according to Eur.J.Org.Chem.2008,994-1004) , 8.71g (0.044mol, 4.4eq) compound shown in formula II (prepared according to WO2014 / 37750), 0.46g (0.0004mol, 0.04eq) tetrakistriphenylphosphine palladium, 12.1g (0.088mol, 8.8eq) potassium carbonate , 80 ml of toluene, 60 ml of ethanol, add to the reactor and stir evenly, slowly raise the temperature to 60-70 ° C for 8 hours, then lower it to 20 ° C, add 100 ml of water, 100 ml of toluene, stir, separate liquid, toluene layer Washed twice with water, dried over anhydrous sodium sulfate, filtered to remove the desiccant, then passed through a silica gel column, the eluate was concentrated to dryness under reduced pressure, and 80 ml of dichloromethane was added to obtain a dichl...

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Abstract

The invention discloses a preparation method of coronene. The preparation method comprises the following steps: coupling reaction: subjecting 1 equivalent of compound shown in a formula I and 4.2-5.6 equivalent of compound shown in a formula II to coupling reaction and converting a reaction product to a compound shown in a formula III; ring closing reaction: subjecting the compound shown in the formula III to ring closing reaction in the presence of acid and converting a reaction product to coronene shown in a formula IV, wherein the formulas I, II, III and IV are shown in the specification. The preparation method has the beneficial effects that the preparation method is simple in process and is easy to operate; the required raw materials are available and are low in costs; therefore the preparation method is suitable for large-scale production.

Description

technical field [0001] The invention belongs to the field of synthesis of organic fluorescent materials, in particular to a preparation method of coronene. Background technique [0002] Coronene is an organic fluorescent material. The maximum absorption wavelength of coronene is 255nm, the maximum emission wavelength is 520nm, and has high quantum efficiency. Therefore, coronene can be used in ultraviolet-charge coupled devices and radar. [0003] At present, the preparation methods about coronene mainly include the following three kinds: [0004] The first kind is the preparation method that JoostT.M.vanDijk discloses in J.Org.Chem.1996,61,1136-1139, and the chemical reaction equation of this method is as follows: [0005] [0006] In this method, the temperature needs to be lowered to -60°C, which is not easy to operate, has many reaction steps and cumbersome operation, so it is not suitable for large-scale production; [0007] The second kind is the preparation meth...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C15/20C07C1/20
CPCC07C1/20C07C41/30C07C15/20C07C43/168Y02P30/20Y02P30/40
Inventor 王占奇
Owner 江苏佳麦化工有限公司
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