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Preparation method of 1-phenyl adamantane and obtained 1-phenyl adamantane

A technology of phenyladamantane and adamantane, which is applied in the field of 1-phenyladamantane, can solve the problems of complex reaction and low yield, and achieve the effect of high reaction yield, low reaction temperature and green production process

Pending Publication Date: 2020-07-24
安徽益瑞德新材料科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] Aiming at the problems of low yield and complex reaction of the existing methods for preparing 1-phenyladamantane, the present invention obtains a safe, green, technically feasible and simple-to-operate method by optimizing the reaction raw materials and using common raw materials to participate in the reaction. The synthetic method of 1-phenyladamantane

Method used

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  • Preparation method of 1-phenyl adamantane and obtained 1-phenyl adamantane
  • Preparation method of 1-phenyl adamantane and obtained 1-phenyl adamantane
  • Preparation method of 1-phenyl adamantane and obtained 1-phenyl adamantane

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Effect test

Embodiment 1

[0043]Under the protection of nitrogen, add magnesium chip (2.64g, 0.11mol), 0.05g iodine, 100ml of anhydrous tetrahydrofuran to the 500ml four-neck flask equipped with mechanical stirrer, reflux condenser, constant pressure dropping funnel, thermometer, and heat to At 60°C, bromobenzene (15.7 g, 0.1 mol) was added dropwise to keep the solvent slightly boiling to obtain 0.1 mol of bromobenzene Grignard reagent. Then continue to drop 150ml tetrahydrofuran solution of 1-bromoadamantane (32.25g, 0.15mol), add anhydrous ferrous chloride (0.635g, 0.005mol), be incubated at 60 degree of reaction 24 hours, as image 3 Shown is ferrous chloride as the reaction mechanism schematic diagram of catalyzer, TLC monitors that reaction finishes, is cooled to room temperature, adds saturated ammonium chloride aqueous solution to quench reaction, extracts organic phase with ethyl acetate, and saturated sodium chloride aqueous solution washes organic phase, Dry over anhydrous magnesium sulfate, ...

Embodiment 2

[0046] Under the protection of nitrogen, magnesium chips (2.64g, 0.11mol), 0.05g iodine, and 100ml of anhydrous ether were added to a 500ml four-necked flask equipped with a mechanical stirrer, a reflux condenser, a constant pressure dropping funnel, and a thermometer, and heated to At 30°C, bromobenzene (15.7 g, 0.1 mol) was added dropwise to keep the solvent slightly boiling to obtain 0.1 mol of bromobenzene Grignard reagent. Then continue to dropwise add the 150ml diethyl ether solution of 1-bromoadamantane (32.25g, 0.15mol), add anhydrous ferrous chloride (0.635g, 0.005mol), be incubated at 35 degree of reaction 24 hours, as image 3 Shown is ferrous chloride as the reaction mechanism schematic diagram of catalyzer, TLC monitors that reaction finishes, is cooled to room temperature, adds saturated ammonium chloride aqueous solution to quench reaction, extracts organic phase with ethyl acetate, and saturated sodium chloride aqueous solution washes organic phase, Dry over an...

Embodiment 3

[0048] Under the protection of nitrogen, add magnesium chip (2.64g, 0.11mol), 0.05g iodine, 100ml of anhydrous tetrahydrofuran to the 500ml four-neck flask equipped with mechanical stirrer, reflux condenser, constant pressure dropping funnel, thermometer, and heat to At 60°C, bromobenzene (15.7 g, 0.1 mol) was added dropwise to keep the solvent slightly boiling to obtain 0.1 mol of bromobenzene Grignard reagent. Then continue to drop 150ml tetrahydrofuran solution of 1-bromoadamantane (32.25g, 0.15mol), add cuprous chloride (0.99g, 0.01mol), and keep warm at 60 degrees for 24 hours, as Figure 4 Shown is cuprous chloride as the reaction mechanism schematic diagram of catalyzer, TLC monitoring reaction finishes, is cooled to room temperature, adds saturated ammonium chloride aqueous solution to quench the reaction, extracts the organic phase with ethyl acetate, and saturated sodium chloride aqueous solution washes the organic phase, Dry over anhydrous magnesium sulfate, filter,...

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Abstract

The invention relates to a preparation method of 1-phenyl adamantane and the obtained 1-phenyl adamantane, and belongs to the technical field of drug synthesis. The preparation method comprises the following steps: taking 1-bromoadamantane and bromobenzene as raw materials, preparing the bromobenzene into a bromobenzene Grignard reagent in an organic solvent, and carrying out a coupling reaction with the 1-bromoadamantane under the catalysis of Lewis acid so as to obtain the target product 1-phenyl adamantane with high yield, and the Lewis acid is a metal chloride. The method is simple in synthesis process, easy to operate and suitable for industrial large-scale production.

Description

technical field [0001] The invention belongs to the technical field of medicine synthesis, and specifically refers to a preparation method of 1-phenyladamantane and the obtained 1-phenyladamantane. Background technique [0002] 1-phenyladamantane ((3r,5r,7r)-1-phenyladamantane) (CAS 780-68-7) and its derivatives are used as a basic chemical intermediate raw material in liquid crystal materials, polymer materials, pharmaceuticals There are large applications in all aspects. The Chinese patent application number is 201110105615.7, and the patent application document with an application publication date of October 19, 2011 discloses (4-(1-adamantyl))phenylhydroquinone and a preparation method thereof. The material in this patent contains phenyladamantane, which has great application value in the preparation of polyarylether resins. The Chinese patent application number is 201580055458.X, and the patent application document with the application publication date of September 26...

Claims

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Application Information

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IPC IPC(8): C07C1/32C07C13/615
CPCC07C1/326C07C2603/74C07C13/615
Inventor 易炜王跃杨洪楠陈俊利
Owner 安徽益瑞德新材料科技有限公司
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