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Synthesis method of 2-phenyl anthracene

A synthesis method and technology of phenylanthracene, which is applied in the field of synthesis of 2-phenylanthracene, can solve the problems of many impurities, difficulty in obtaining raw materials, and high production cost, and achieve the effects of high yield, reduced production cost, and low environmental hazards

Pending Publication Date: 2022-06-07
XIAN RUILIAN NEW MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The purpose of the present invention is to solve the problems that the current known synthesis process of 2-phenylanthracene is difficult to obtain raw materials, high production cost, large waste, many impurities, difficult to control the reaction end point, only suitable for small-scale preparation, and difficult to realize industrial production.

Method used

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  • Synthesis method of 2-phenyl anthracene
  • Synthesis method of 2-phenyl anthracene
  • Synthesis method of 2-phenyl anthracene

Examples

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Embodiment 1

[0024] This embodiment provides an industrialized production method of 2-phenylanthracene.

[0025] The synthesis process is as follows:

[0026] To a 1L three-necked round-bottomed flask, 286 mL of tetrahydrofuran, 28.60 g (0.1 mol) of 2,3-dibromonaphthalene were successively added, the temperature was lowered to -80°C to -70°C with stirring, and 60 mL of n-butyllithium (2mol / L, 0.12mol), stir for 0.5h, add 10.97g (0.15mol) of N,N-dimethylformamide, add dropwise, keep at -85~-70°C and stir for 3h, naturally heat up to -20°C, add hydrochloric acid to acidify to pH =7, naturally rise to room temperature, concentrate under reduced pressure until the inner temperature is equal to 45°C, add 286 mL of toluene to dilute, separate the phases, concentrate the organic phase at normal pressure to the remaining 30 mL of the system, add 143 mL of n-heptane, put it in the refrigerator for 3 hours of freezing and crystallization, Filter and bake to constant weight to obtain 20.30 g of off-...

Embodiment 2

[0039] This embodiment provides an industrialized production method of 2-phenylanthracene.

[0040] The synthesis process is as follows:

[0041] To a 1L three-necked round-bottomed flask, 286 mL of tetrahydrofuran and 28.60 g (0.1 mol) of 2,3-dibromonaphthalene were successively added, the temperature was lowered to -80°C to -70°C with stirring, and 90 mL of n-butyllithium (2mol / L, 0.18mol), stir for 0.5h, add 18.26g (0.25mol) of N,N-dimethylformamide, add dropwise, keep at -85~-70°C, stir for 3h, naturally heat up to -20°C, add hydrochloric acid to acidify to pH =7, naturally rise to room temperature, concentrate under reduced pressure until the inner temperature is equal to 45°C, add 286 mL of toluene to dilute, separate the phases, concentrate the organic phase at normal pressure to the remaining 30 mL of the system, add 143 mL of n-heptane, put it in the refrigerator for 3 hours of freezing and crystallization, Filter and bake to constant weight to obtain 19.88 g of an o...

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PUM

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Abstract

The invention provides a synthesis method of 2-phenyl anthracene, which comprises the following steps: reacting 2, 3-dibromonaphthalene with n-butyllithium and N, N-dimethylformamide to generate 2-formyl-3-bromonaphthalene; 2-formyl-3-bromonaphthalene and styrene are subjected to a Heck reaction, and 2-formyl-3-styryl naphthalene is generated; the 2-formyl-3-styryl naphthalene, chloromethyl ether triphenylphosphine salt and potassium tert-butoxide are subjected to a Wittig reaction, and 2-methoxyvinyl-3-styryl naphthalene is generated; and carrying out ring closing on the 2-methoxyvinyl-3-styryl naphthalene through methanesulfonic acid to prepare the 2-phenyl anthracene. The synthesis method of 2-phenyl anthracene provided by the invention adopts the raw materials with low price, the reaction process and post-treatment are simple, the harm to the environment is small, the production cost is reduced, the yield is high, and the synthesis method is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and relates to a method for synthesizing 2-phenylanthracene. Background technique [0002] 2-phenylanthracene contains multiple strong active sites and can react with N-chlorosuccinimide, N-bromosuccinimide, dibromohydantoin, bromine, etc. The expansion of the molecular structure can be achieved by introducing the corresponding halides at the 10th and 5th positions of 2-phenylanthracene, and then introducing other molecular fragments through Suzuki reaction, Buchwald reaction, Heck reaction and Ullmann reaction. Based on the above characteristics, 2-phenylanthracene, as a derivative synthesized as an intermediate, is widely used in the synthesis of materials with conjugated structures, and has a wide range of applications in field-effect transistors, organic light-emitting diodes and other fields. [0003] At present, the common synthesis methods of 2-phenylanthracene, one is to use 2-...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C15/60C07C1/20
CPCC07C1/20C07C41/30C07C45/68C07C45/004C07C2603/24C07C15/60C07C43/166C07C47/548C07C47/55Y02E10/549
Inventor 张江春贾小伟毛涛王小伟张珍
Owner XIAN RUILIAN NEW MATERIAL CO LTD
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