Preparation method of CF2O-contained monomer liquid crystal compound

A technology of difluoromethoxy ether and liquid crystal compounds, which is applied in the preparation of organic compounds, chemical instruments and methods, liquid crystal materials, etc., can solve the problems of low price, harsh reaction conditions and high price.

Active Publication Date: 2014-08-13
SHANGHAI CHEMSPEC CORP +1
View PDF6 Cites 17 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method has few reaction steps, and the crude product yield is as high as 70%. The price of the reagents used is relatively low, the product is easy to purify, and has good industrialization prospects.
[0008] Although there are multiple methods for synthesizing difluoromethoxy ether bridging liquid crystals, the reaction conditions

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Preparation method of CF2O-contained monomer liquid crystal compound
  • Preparation method of CF2O-contained monomer liquid crystal compound
  • Preparation method of CF2O-contained monomer liquid crystal compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment approach

[0082] The invention provides a bridge containing difluoromethoxyether (CF 2 O) the preparation method of the monomer liquid crystal compound, specifically refers to the compound of formula V structure,

[0083]

[0084] Wherein said R is selected from C1-C9 substituted or unsubstituted alkyl groups, alkoxy groups, ester groups or combinations thereof; preferably, said C1-C9 substituted or unsubstituted alkyl groups are selected from CH 3 , C 2 h 5 , C 3 h 7 , C 4 h 9 , C 5 h 11 , or CH 2 OCH 3 ; Alkoxy group is selected from OR', wherein said R' is C1-C8 alkyl, and said ester group is selected from COOR "or CH 2 COOR" ester group, wherein said R" is a C1-C8 alkyl group.

[0085] which stated selected from phenyl, cyclohexyl and derivatives thereof or combinations thereof.

[0086] which stated selected from phenyl, cyclohexyl or combinations thereof, wherein X 1 、X 2 、X 3 、X 4 Selected from F, Br, Cl or H and alkoxy or ester group; alkoxy group is selec...

Embodiment 1

[0125] Preparation of O-3,4,5-trifluorobenzene-2,6-difluoro-4-bromobenzenethiocarbamate

[0126] Under the protection of nitrogen, add 61.8g of 3,5-difluorobromobenzene and 100mL THF into a 1L four-necked bottle, cool the system to -50°C, add 359.8g of 10% LDA (lithium diisopropylamide) dropwise, and drop- Stir at 50°C for 1 hour, dissolve 34.9g of zinc chloride in 200mLTHF and add to the system and stir for 30min; add 21.6g of copper chloride and 86.8g of O-3,4,5-trifluorobenzene-chlorothioformate into 1L Add 200mL THF to the mouth bottle, add the prepared zinc reagent to the reaction system at 20°C, there is obvious exotherm, react for 4 hours after dripping, add 250mL of 10% hydrochloric acid to the system, fully acidify the system to pH<1, and let stand to separate layer, the aqueous phase was extracted twice with 100 mL of tertiary methyl ether and the organic phase was precipitated to obtain 130.5 g of a yellow crude product, and recrystallized from methanol to obtain 10...

Embodiment 2

[0130] Preparation of O-3,4,5-trifluorobenzene-2,3-difluoro-4-chlorobenzenethiocarbamate

[0131] Under nitrogen protection, add 110.9g of 2,3-difluoro-4-chloroiodobenzene, 52.5g of zinc powder and 440mL THF into a 1L four-necked bottle, and prepare zinc reagent by reflux reaction; mix 21.6g of cuprous cyanide with O-3 , Add 109.6g of 4,5-trifluorobenzene-chlorothioformate into a 1L four-necked bottle and add 200mL THF. Add the prepared zinc reagent into the reaction system at 20°C. There is obvious exotherm, and react for 4 hours after dropping . Add 250mL of water to the system, let stand to separate the layers, extract the water phase twice with 100mL of tertiary methyl ether and combine the organic phase for desolventization to obtain 139.8g of the yellow crude product, 115.8g of the target product was obtained by methanol recrystallization, and the content detected by gas chromatography was 98.3 %, the yield is 84.7%.

[0132] h 1 NMR (300MHz, CD 3 Cl): δ6.81-6.91(m,2...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

PropertyMeasurementUnit
Melting pointaaaaaaaaaa
Melting pointaaaaaaaaaa
Melting pointaaaaaaaaaa
Login to view more

Abstract

The invention provides a preparation method of a CF2O-contained monomer liquid crystal compound. The preparation method comprises the following steps of (1) with a compound with a structure as shown in the formula I as a raw material, reacting under the catalytic action of a zinc reagent and copper salt and in the existence of a solvent to generate a compound with a structure as shown in the formula II; (2) enabling the compound with the structure as shown in the formula II and a fluorinated reagent to be subjected to fluoridation in the existence of the solvent to generate a compound with a structure as shown in the formula III; (3) enabling the compound with the structure as shown in the formula III and boric acid as shown in the formula IV to be subjected to SUZUKI coupled reaction in the existence of the solvent to obtain the CF2O-contained monomer liquid crystal compound with a structure as shown in the formula V, wherein the CF2O-contained monomer liquid crystal compound with a structure as shown in the formula V is as shown in the specification.

Description

technical field [0001] The invention relates to a preparation method of a monomer liquid crystal compound, in particular to a method containing a difluoromethoxyether bridge (CF 2 O) The preparation method of the monomer liquid crystal compound Background technique [0002] In recent years, wide viewing angle and high contrast IPS-TFT mode liquid crystal display technology has been widely used in high-end display fields such as LCD TVs. IPS-TFT mode liquid crystal display requires the use of large Δε (dielectric anisotropy) value liquid crystal material. Using a liquid crystal material with a large Δε value in the traditional TN-TFT mode can effectively reduce the driving voltage and power consumption, which is beneficial to portable display. [0003] The research on the application of mixed liquid crystal formulations shows that after introducing difluoromethoxy ether bridge bonds into the liquid crystal molecular skeleton, it can increase the Δε value, reduce the rotatio...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
IPC IPC(8): C07C43/225C07C41/30C07C69/08C07C67/293C09K19/20
CPCC07C41/30C07C43/225C07C67/293C07C69/08C09K19/20
Inventor 曾原吴华锋张麦旋彭勇焦海华常文化
Owner SHANGHAI CHEMSPEC CORP
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap