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A kind of biphenyl compound and its application in the preparation of 1,8-dibromopyrene

A kind of technology of dibromopyrene and biphenyl, applied in 1 field, can solve the problems such as trivial separation, many selective sites for bromination reaction, increasing the risk of pyrene compound contact and the like

Active Publication Date: 2021-02-26
西安穿越光电科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the existing preparation method of 1,8-dibromopyrene, the method of pyrene bromination is adopted. Since the pyrene ring is relatively active, there are many sites for the bromination reaction, so it is difficult to control the bromination reaction at the designated position, and During the reaction process, more polybrominated products will be generated, and the separation is cumbersome
[0003] In addition, since pyrene is a condensed ring aromatic hydrocarbon, there is a potential for great harm to the human body. The reaction raw materials and products of the prior art are all pyrene compounds, and the products need cumbersome purification, which greatly increases the number of operators and pyrene compounds. Compound Exposure Risks

Method used

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  • A kind of biphenyl compound and its application in the preparation of 1,8-dibromopyrene
  • A kind of biphenyl compound and its application in the preparation of 1,8-dibromopyrene
  • A kind of biphenyl compound and its application in the preparation of 1,8-dibromopyrene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] The synthetic route is as follows:

[0038]

[0039] (1) Nitrification reaction:

[0040]

[0041] In a 1000ml three-necked flask, add 100ml of dichloromethane, 200ml of acetic anhydride, 31.2g (0.1mol) of 3,3'-dibromo-1,1'-biphenyl, cool down to 5-10°C, and slowly add 58.1 A mixed solution of gram (0.6mol) 65% nitric acid and 41.3 grams (0.4mol) 95% sulfuric acid, keep at 5-10°C for 2 hours after adding, then slowly rise to 25°C and keep for 2 hours, add water and dichloromethane to separate the liquid , the organic layer was washed with water, washed with sodium hydroxide solution, and then washed with water to neutrality, after the organic layer was dried with calcium chloride, concentrated to dryness, separated by silica gel column chromatography, washed with petroleum ether:ethyl acetate=9:1 (volume ratio) After separation, 9.6 g of 3,5'-dibromo-2,2'-dinitro-1,1'-biphenyl was obtained with a yield of 23.88%.

[0042] The obtained 3,5'-dibromo-2,2'-dinitro-1...

Embodiment 2

[0067] The synthetic route is as follows:

[0068]

[0069] Synthesis of steps (1) to (3) Referring to Example 1, 3,5'-dibromo-2,2'-diiodo-1,1'-biphenyl was synthesized.

[0070] (4) Substitution reaction:

[0071]

[0072] 500 ml three-necked flask, nitrogen protection, add 5.64 g (0.01 mol) 3,5'-dibromo-2,2'-diiodo-1,1'-biphenyl, 100 ml dry tetrahydrofuran, cool to -85 °C , slowly add 12.5 ml (0.02mol) of 1.6M butyllithium n-hexane solution dropwise, keep at -85°C for 30 minutes after the addition, then add 2.92 grams (0.04mol) of N,N-dimethylformamide, and complete the addition Slowly rise to room temperature, add water solution, wash the organic layer with water, dry over sodium sulfate, concentrate to dryness, separate by silica gel column chromatography, petroleum ether: ethyl acetate = 2: 1 (volume ratio) elution separation, to obtain 3,5 1.86 g of '-dibromo-2,2'-diformyl-1,1'-biphenyl, yield 50.5%.

[0073] The obtained 3,5'-dibromo-2,2'-diformyl-1,1'-biphenyl...

Embodiment 3

[0088] The synthesis method refers to Example 1, except that in the substitution reaction in step (4), butyl vinyl ether is replaced with benzyl vinyl ether to prepare 1,8-dibromopyrene.

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Abstract

The invention discloses a biphenyl compound and its application in preparing 1,8-dibromopyrene.

Description

technical field [0001] The invention belongs to the field of organic material synthesis, and in particular relates to a preparation method of 1,8-dibromopyrene. Background technique [0002] 1,8-Dibromopyrene is an important intermediate of organic electroluminescent materials. In the existing preparation method of 1,8-dibromopyrene, the method of pyrene bromination is adopted. Since the pyrene ring is relatively active, there are many sites for the bromination reaction, so it is difficult to control the bromination reaction at the designated position, and During the reaction, more polybrominated products will be generated, and the separation is tedious. [0003] In addition, since pyrene is a condensed ring aromatic hydrocarbon, there is a potential for great harm to the human body. The reaction raw materials and products of the prior art are all pyrene compounds, and the products need cumbersome purification, which greatly increases the number of operators and pyrene comp...

Claims

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Application Information

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IPC IPC(8): C07C201/08C07C205/12C07C209/36C07C211/52C07C17/093C07C25/18C07C41/22C07C43/176C07C17/35C07C25/22C07C45/00C07C47/55
CPCC07C17/093C07C17/35C07C25/18C07C25/22C07C41/22C07C43/176C07C45/00C07C47/55C07C201/08C07C205/12C07C209/36C07C211/52
Inventor 李现伟
Owner 西安穿越光电科技有限公司
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