1,3-benzodiazole-containing compounds connected in series with gem-difluoromethylene groups and their synthesis methods

A technology of difluoromethylene and benzodiazole, applied in the field of 1,3-benzodiazole-containing compounds, can solve problems such as not yet reported, and achieve the effects of high research and application value and easy operation

Inactive Publication Date: 2011-11-30
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] For the synthetic method of the compound containing 1,3-benzodiazole i

Method used

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  • 1,3-benzodiazole-containing compounds connected in series with gem-difluoromethylene groups and their synthesis methods
  • 1,3-benzodiazole-containing compounds connected in series with gem-difluoromethylene groups and their synthesis methods
  • 1,3-benzodiazole-containing compounds connected in series with gem-difluoromethylene groups and their synthesis methods

Examples

Experimental program
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Effect test

Embodiment 1

[0024] Example 1: Under nitrogen protection, 414 mg (1.5 mmol) ethyl 4-iodobenzoate and 248 mg (1 mmol) 2-bromodifluoromethane were added to a 25 ml two-neck bottle equipped with a magnet Base 1,3-benzoxazole, 2 ml dimethyl sulfoxide, 64 mg (1 mmol) copper powder, react at room temperature for 4 hours, stop the reaction, cool the reaction solution to room temperature, and directly use silica gel column chromatography to separate and purify , 32 mg of the product was obtained with a yield of 10%. The structure of this compound is:

[0025]

[0026] Chinese name: ethyl 4-(2-benzoxazolyl)difluoromethylbenzoate

[0027] English name: 4-(Benzooxazol-2-yl-difluoro-methyl)-benzoic acid ethyl

[0028] Molecular weight: 317.09

[0029] Appearance: white solid

[0030] Melting point: 59-61 degrees Celsius

[0031] H NMR spectrum (500 MHz, CDCl 3 ) chemical shift (in ppm): δ 8.17 (d, J = 8.5 Hz, 2H, ArH), 7.80 (d, J = 8.4 Hz, 3H, ArH), 7.59 (d, J = 8.1 Hz, 1H, ArH), 7.3...

Embodiment 2

[0036]Example 2: Under nitrogen protection, 414 mg (1.5 mmol) ethyl 4-iodobenzoate, 248 mg (1 mmol) 2-bromodifluoro Methyl 1,3-benzoxazole, 10 ml dimethylformamide, 64 mg (1 mmol) copper powder, stop the reaction after 4 hours at room temperature, cool the reaction solution to room temperature, and directly use silica gel column chromatography After separation and purification, 89 mg of the product was obtained with a yield of 28%.

Embodiment 3

[0037] Example 3: Under nitrogen protection, 1.1 g (4 mmol) ethyl 4-iodobenzoate, 2 g (8 mmol) 2-bromodifluoro Methyl 1,3-benzoxazole, 35 ml dimethylformamide, 1.2 g (18.4 mmol) copper powder, stop the reaction after 8 hours at room temperature, cool the reaction solution to room temperature, and directly use silica gel column chromatography After separation and purification, 0.98 g of the product was obtained with a yield of 77%.

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Abstract

The invention relates to a compound containing 1,3-benzodiazole connected in series with gem-difluoromethylene groups and a synthesis method thereof. The structural formula of this type of compound is: where R is: -COOEt-Ph, -COOCH3-Ph, -NO2-Ph, Ph, -OCH3-Ph, -CH3-Ph, -CH3-Ph, -NO2-Ph, Pyridine, (Z)-CH=CHCOOEt, (E)-CH=CHCOOEt or (E)-CH=CHPh; X is: O, S or NCH2CH2CH2CH3. The compounds containing 1,3-benzodiazoles in tandem with gem-difluoromethylene groups of the present invention exhibit unique properties in novel liquid crystal materials, so efficient synthesis of such compounds becomes very meaningful. The synthesis method has the characteristics of simple operation, short steps and convenient post-processing.

Description

technical field [0001] The invention relates to a compound containing 1,3-benzodiazole in series with gem-difluoromethylene groups and a preparation method thereof. Background technique [0002] The rapid development of liquid crystal display has replaced the traditional cathode ray tube display and has become the mainstream product in the field of information display, which directly affects the rapid development of liquid crystal materials. With the advancement of liquid crystal displays into household appliances, especially the successful application of household large-screen TVs, there are higher requirements for the quality of liquid crystal materials. One is that the various monomers that make up the mixed liquid crystal are required to have a wider liquid crystal phase transition temperature range. The second is to reduce the viscosity of the liquid crystal material as much as possible to improve the response speed of the display. The third is to increase the dielect...

Claims

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Application Information

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IPC IPC(8): C07D263/56C07D413/06C07D235/10C07D277/64C09K19/34C09K11/06
Inventor 蒋海珍杨昆郝健陆文峻万文
Owner SHANGHAI UNIV
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