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Preparation method of CF2O-containing compound, and intermediate compound and preparation method thereof

A compound and catalyst technology, applied in the field of preparation of CF2O-containing compounds, intermediates and preparation thereof, can solve the problems of unfavorable scale-up production, low product yield and high production cost

Active Publication Date: 2014-12-24
LIANHE CHEM TECH +4
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] In order to overcome the reaction in the preparation method of the existing 4-(4-n-propyl)phenyl-3,5-difluoro-1',1'-difluorobenzyl-3,4,5-trifluorophenyl ether The conversion rate is low, the product yield is low, the atom economy is poor, the production cost is high, and it is not conducive to the defects such as large-scale production, while providing the CF-containing 2 Preparation method, intermediate and preparation method of O compound

Method used

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  • Preparation method of CF2O-containing compound, and intermediate compound and preparation method thereof
  • Preparation method of CF2O-containing compound, and intermediate compound and preparation method thereof
  • Preparation method of CF2O-containing compound, and intermediate compound and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 14

[0075] The preparation of embodiment 14-bromo-3,5-difluoro-4'-propylbiphenyl

[0076]Add 420g of tetrahydrofuran (THF) and 185g (0.80mol) of 3,5-difluoro-4'-propylbiphenyl into a 2000mL four-neck flask, replace with nitrogen for 3 times, and cool down to -50 after the replacement is completed. ℃, after cooling down, slowly add 400mL (1.00mol, 2.5mol / L) of n-butyllithium n-hexane solution dropwise. After the addition, the temperature was kept for 2 hours, and after the heat preservation was completed, the temperature was naturally raised to room temperature. Add 365g of an aqueous solution of hydrochloric acid (the mass percent refers to the percentage of the mass of hydrogen chloride in the total mass of the aqueous solution of hydrochloric acid) with a mass percentage of 10%, evaporate the solvent, then extract with 200g×3 petroleum ether, and combine the organic layers. Add 50 g of anhydrous magnesium sulfate, stir for 10 minutes, pass through a 40 g silica gel column, and ...

Embodiment 24

[0077] Preparation of embodiment 24-bromo-3,5-difluoro-4'-propylbiphenyl Grignard reagent

[0078] Add 21.2g (0.88mol) of magnesium chips, 0.0227g of iodine and 200g of tetrahydrofuran (THF) into a 1000mL four-neck flask, replace with nitrogen three times, stir at 20°C, and dropwise add 4-bromo-3,5-bis Fluoro-4'-propyl biphenyl crude product 23.8g (0.074mol) and tetrahydrofuran (THF) 100g mixed solution. Stir after the dropwise addition, and after the color of the solution fades, add dropwise a mixture of 212.6g (0.661mol) of crude 4-bromo-3,5-difluoro-4'-propylbiphenyl and 200g tetrahydrofuran (THF) at 20°C . After the dropwise addition, the temperature was kept, and the dropwise addition time and the heat preservation time were 4 hours in total. Then 4-bromo-3,5-difluoro-4'-propylbiphenyl Grignard reagent is obtained. It was directly used in the next reaction without purification.

Embodiment 35

[0079] Example 35- Preparation of (bromo-difluoro-methoxy)-1,2,3-trifluorobenzene

[0080] Add 600 g of N,N-dimethylacetamide (DMAC) into a 2000 mL four-necked bottle. At 20°C, 11.5 g (0.5 mol) of sodium and 4.8 g (0.2 mol) of sodium hydride were sequentially added. After stirring for 1 hour, start to add dropwise a mixture of 200 g (1.35 mol) of 3,4,5-trifluorophenol and 200 g of N,N-dimethylacetamide (DMAC). After the dropwise addition, keep stirring for 2 hours. Start to feed 337g (1.62mol) of difluorodibromomethane. After the dropwise addition, keep stirring for 6 hours. After keeping warm, pour the reaction solution into a 5000mL glass reactor, add 1000g methyl tert-butyl ether and 2000g water, stir, and divide After the solution was extracted with 200g×2 methyl tert-butyl ether, the combined organic layers were washed with 200g×3 water, and after washing, the methyl tert-butyl ether was evaporated (methyl tert-butyl ether can be recycled and used mechanically), and petr...

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Abstract

The invention discloses a preparation method of a CF2O-containing compound, and an intermediate compound and a preparation method thereof. The preparation method of a CF2O-containing compound, provided by the invention, comprises the following step: in solvent, in the presence of a catalyst, performing coupling reaction on 5-(bromo-difluoro-methoxy)-1,2,3-trifluorobenzene shown as Formula 1 and a Grignard reagent 3,5-difluoro-4'-propylbiphenyl-4-magnesium bromide shown as Formula 2, thus obtaining 4-(4-n-propyl)phenyl-3,5-difluoro-1',1'-difluorobenzyl-3,4,5-trifluorophenyl ether shown as Formula 3. The preparation method provided by the invention is simple to operate, mild in reaction conditions, convenient in posttreatment steps, high in reaction conversion rate, high in atom economy, friendly to environment, favorable in product purity and suitable for industrial production.

Description

technical field [0001] The present invention relates to CF containing 2 Preparation method, intermediate and preparation method of O compound. Background technique [0002] Difluoromethoxy bridge (CF 2 O) The monomeric liquid crystal compound has the characteristics of high dielectric anisotropy and low viscosity. This compound liquid crystal is widely used in TFT-LCD mixed liquid crystals. Due to the preparation process of the monomeric liquid crystal compound containing difluoromethoxy central bridge bonds Complex, expensive and difficult to industrialize. In this way, a new method to prepare difluoromethoxy center bridge (CF 2 O) monomer liquid crystal compounds, it becomes a very urgent task. [0003] The compound 4-(difluoro(3,4,5-trifluorophenoxy)methyl)-3,5-difluoro-4'-propyl-1,1'-biphenyl involved in the present invention is A representative difluoromethoxy center-bridged monomer. Contains CF 2 The difficulty in the synthesis of O compounds is how to convenien...

Claims

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Application Information

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IPC IPC(8): C07C43/225C07C41/30C07C41/16C07F3/02
Inventor 郭章红顾建超李强张兴王萍樊小彬
Owner LIANHE CHEM TECH
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