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Improved synthetic method of aryl substituted naphthopyran photochromic compound

A kind of technology of naphthopyrans, synthetic method

Active Publication Date: 2014-05-07
成都宇西医药技术有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0012] Although a variety of methods for preparing naphthopyran photochromic compounds have also been reported in the prior art, these methods have inherent low yields and are unfavorable for industrial applications. The inventor aims to improve the above-mentioned defects. The method of the prior art, in order to obtain a kind of method for synthesizing aryl substituted naphthopyran photochromic compound with high yield, thereby satisfy the general demand of the development of high technology to photochromic compound, and eliminate the unnecessary Ideal factors to achieve the goal of greatly improving material utilization and product yield

Method used

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  • Improved synthetic method of aryl substituted naphthopyran photochromic compound

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preparation example 1

[0033] Preparation Example 1: Synthesis of Naphthopyran-2-one

[0034] Add 1mol of 2-hydroxy-1-naphthaldehyde, 2.2mol of anhydrous acetic anhydride and 2.1mol of anhydrous sodium acetate in the reaction kettle, heat up to reflux for 5 hours, after the reaction is completed, cool the reaction solution to room temperature, add Aqueous sodium carbonate solution with a mass concentration of 12% adjusted the pH to neutral to remove unreacted acetic anhydride, then added chloroform to dissolve the solid product, separated the liquid and dried with anhydrous magnesium sulfate, filtered and rotary evaporated, then added petroleum ether Promote the formation of precipitates, filter again, and dry to obtain the intermediate naphthopyran-2-one with a yield of 90% and a purity of 94.7% as detected by high performance liquid chromatography.

Embodiment 1

[0035] Example 1: Synthesis of 2,2-bis(3-methylphenyl)naphthopyran

[0036] Under a nitrogen atmosphere, add 0.6mol of magnesium chips to the reaction kettle, then dropwise add a mixture containing 1.2mol of 3-methyl-1-bromobenzene and 50ml of THF, gradually raise the temperature to reflux reaction, and react until the reaction of magnesium chips is complete, stop Reaction to obtain the Grignard reagent; in the prepared Grignard reagent, add 0.2mol of naphthopyran-2-one, add 0.02mol of tetrabutylphosphine bromide and 180ml of 1-butyl-3- Methylimidazolium chloride salt, heated at 60°C and kept for 7 hours. After the reaction, add ammonium chloride aqueous solution with a mass concentration of 22% for hydrolysis, then add ether for extraction, dry with anhydrous magnesium sulfate, and undergo recrystallization and column chromatography. Purification gave the target product with a yield of 85.2% and a purity of 98.7% (HPLC).

Embodiment 2

[0037] Example 2: Synthesis of 2,2-bis(3-trifluoromethylphenyl)naphthopyran

[0038] Under a nitrogen atmosphere, add 0.8mol magnesium chips to the reaction kettle, then dropwise add a mixed solution containing 1.6mol 3-trifluoromethyl-1-bromobenzene and 65ml THF, gradually raise the temperature to reflux reaction, and react until the magnesium chips are completely reacted , stop the reaction to obtain the Grignard reagent; in the prepared Grignard reagent, add 0.25mol of naphthopyran-2-one, add 0.015mol of tetrabutylphosphine bromide and 250ml of 1-butyl- 3-Methylimidazolium chloride, heated at 70°C and kept for 6.5 hours. After the reaction, add ammonium chloride aqueous solution with a mass concentration of 22% for hydrolysis, then add ether for extraction, dry with anhydrous magnesium sulfate, recrystallize and Purified by column chromatography to obtain the target product with a yield of 86.3% and a purity of 98.9% (HPLC).

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Abstract

The invention relate to a synthetic method of an aryl substituted naphthopyran photochromic compound. The synthetic method comprises the following two steps of synthesizing naphthopyran-2-ketone; and synthesizing the aryl substituted naphthopyran photochromic compound. According to the invention, the purpose of simply and efficiently preparing the aryl substituted naphthopyran photochromic compound is realized in a reaction environment in the presence of ionic liquid based on quaternary phosphonium salt as a catalyst in the second step, so that the synthetic method suitable for industrialized production is provided for the preparation of the aryl substituted naphthopyran photochromic compound. The synthetic method disclosed by the invention has the advantages of potential industrialized prospect and market value.

Description

technical field [0001] The invention relates to a preparation method of a photochromic compound, in particular to an improved synthesis method of an aryl-substituted naphthopyran photochromic compound, and belongs to the field of organic chemical synthesis. Background technique [0002] Photochromism [Photochromism] refers to the color change of a substance under the irradiation of light of a certain wavelength, and then returns to its original color under the irradiation of light of another wavelength or heat. Naphthopyran compounds are the most common photochromic compounds among pyran compounds, and are widely used. For example, 2,2-diphenylnaphthopyran has been commercialized in the early 1990s. change. [0003] There are roughly three conventional methods for synthesizing naphthopyrans in the prior art. The first is to utilize the Kabbe synthesis method, see "Synthesis and Reactivity of some 4-Bromo-2H-Chromenes and 2H-Thiochromenes", Christopher D.Gabbutt et al., Tet...

Claims

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Application Information

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IPC IPC(8): C07D311/92
CPCC07D311/92
Inventor 章方军
Owner 成都宇西医药技术有限公司
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