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Preparation method of triphenylene derivative

A technology for triphenylene and derivatives, applied in the field of preparation of triphenylene derivatives, can solve the problems of not being an industrialized production method, low efficiency and high cost

Active Publication Date: 2021-03-30
SHANGHAI CHEMSPEC CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] This method needs to prepare 2-biphenyl pinacol borate, needs to use noble metal catalyst, and cost is higher; Simultaneously the cost of raw material p-bromoiodobenzene is also significantly higher than p-dibromobenzene, and this causes the raw material cost of this scheme to be higher The efficiency of the scholl reaction that uses ferric chloride system to carry out is lower simultaneously, and yield generally can only reach about 40~50% in the literature report; Therefore also not ideal industrialized production method

Method used

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  • Preparation method of triphenylene derivative
  • Preparation method of triphenylene derivative
  • Preparation method of triphenylene derivative

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preparation example Construction

[0059] The present invention provides a preparation method of triphenylene derivatives, comprising: subjecting the compound of formula 4 to ring-closing reaction in the presence of an acid, an initiator and an oxidizing agent to provide the compound of formula 5, and the reaction equation is as follows:

[0060]

[0061] Wherein, R is selected from Cl, Br, OR', and R' is selected from H, C1-C5 alkyl, benzyl. For the compound of formula 4, there is a problem of low reactivity when it is used as a reaction substrate, so the commonly used scheme of oxidative ring closure by oxidizing agent is difficult to realize efficiently on this type of substrate. However, in the present invention, by introducing an initiator to excite the intermediate state of the reaction, the reaction can smoothly cross the reaction energy barrier, thereby successfully completing the ring closure reaction.

[0062] In the present invention, the "alkyl group" generally refers to a saturated aliphatic gro...

Embodiment 1

[0101] Preparation of biphenyl-2-boronic acid:

[0102] Add 28.8g (1.2mol) metal magnesium and a grain of iodine to a 2000ml four-necked bottle, dissolve 233g (1.0mol) of 2-bromobiphenyl in 1100ml THF, add it to a constant pressure dropping funnel, and add dropwise 50ml of this mixture In the reaction bottle, heat to initiate the format, after the initiation, control the temperature between 50°C and 55°C and add the remaining 2-bromobiphenyl solution dropwise. Lower the temperature of the system to -40°C, add dropwise a solution of 135.2g (1.3mol) trimethyl borate dissolved in 240ml THF, control the temperature to less than -25°C, keep warm at this temperature for 1 hour after the dropwise addition, and then naturally rise to room temperature, Add hydrochloric acid dropwise to adjust PH = 1, separate layers, distill off THF under reduced pressure, add water for beating, filter with suction, add petroleum ether to the filter cake for beating, and dry to obtain 163g of biphenyl-...

Embodiment 2

[0105] Preparation of biphenyl-2-boronic acid:

[0106]Add 233g (1.0mol) of 2-bromobiphenyl and 1400ml THF into a 5000ml four-necked bottle, add butyllithium solution (1.2mol) dropwise between -50°C and -65°C, keep warm for 1 hour after dropping, and monitor by gas chromatography Raw materials are reacted. Add 244.5g (1.3mol) triisopropyl borate dropwise at -50°C, control the temperature below -5°C, keep warm at this temperature for 1 hour after the dropwise addition, then naturally rise to room temperature, add hydrochloric acid dropwise to adjust PH=1, and separate layers , THF was evaporated under reduced pressure, water was added for beating, suction filtration was added, and toluene was added for beating the filter cake, and 169 g of biphenyl-2-boric acid was obtained by drying, the liquid chromatography content was 99.3%, and the yield was 85.5%.

[0107]

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Abstract

The invention relates to the field of organic chemistry, and in particular, relates to a preparation method of a triphenylene derivative. The invention provides the preparation method of the triphenylene derivative, wherein the method comprises the step: carrying out cyclization reaction on a compound represented by a formula 4 in the presence of acid, an initiator and an oxidant to provide a compound represented by a formula 5. According to the preparation method of the triphenylene derivative, provided by the invention, arylation reaction is carried out by using the acid and the oxidant, sothat side reactions generated in the reaction are few, the overall conversion rate of the reaction is high, and the raw materials are economical and practical; and in addition, the whole reaction route has high reaction yield and is convenient for industrial production and operation, and good industrialization prospects are realized.

Description

technical field [0001] The invention relates to the field of organic chemistry, in particular to a preparation method of triphenylene derivatives. Background technique [0002] Triphenylene derivatives are important raw materials for a new class of organic light-emitting semiconductor materials, and are important raw materials for self-luminescence in OLEDs. In the existing literature reports, the synthesis route of this type of compound is long, the raw materials are not easy to prepare, the reaction impurities are more, the quality control is difficult, and the overall yield is low. Especially in the step of aromatization, the yield is generally not high, the conversion rate is low, the side reactions are complicated, and the purification is difficult, resulting in a higher overall synthesis cost. [0003] There are mainly the following routes to synthesize this type of compound in the existing data: [0004] Route 1 (US20100072887, PCT Int.Appl., 2013085243, PCT Int.App...

Claims

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Application Information

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IPC IPC(8): C07C41/18C07C43/20C07C17/357C07C25/22C07C37/06C07C39/12
CPCC07F5/025C07C17/32C07C41/30C07C37/18C07C41/18C07C17/357C07C37/06C07C25/18C07C43/205C07C39/15C07C43/20C07C25/22C07C39/12
Inventor 李桂云曾原姚腾飞陈学宇何立袁云龙
Owner SHANGHAI CHEMSPEC CORP
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