Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Preparation method of propyl o-fluorobenzene compound

The technology of a compound and fluorobenzene is applied in the field of preparation of propyl-o-fluorobenzene compounds, can solve the problems of low product purity, polluted fluorine impurities, high raw material price, etc., and achieves low price, low cost and reduced raw material cost. Effect

Active Publication Date: 2012-12-05
VALIANT CO LTD
View PDF6 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0018] The technical problem to be solved by the present invention is to provide a simple, efficient and environmentally friendly method to prepare propyl-o-fluorobenzene compounds, so as to solve the problems in the prior art of high raw material prices, low product purity, serious pollution or large fluorine-removing impurities , to meet the requirements of mass industrialization of such products

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 propyl o-fluorobenzene compound
  • Preparation method of propyl o-fluorobenzene compound
  • Preparation method of propyl o-fluorobenzene compound

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0059] A kind of preparation method of propyl-o-fluorobenzene compound, first make raw material compound I into lithium reagent, then lithium reagent and allyl chloride or allyl bromide take place coupling reaction under the catalysis of copper, the product obtained is passed through Catalytic hydrogenation can give propyl-o-fluorobenzene compounds.

[0060] Wherein, the structural formula of the raw material compound I is:

[0061]

[0062] The R is C 0 ~C 5 straight chain alkyl, said n is 0 or 1 or 2, said m is 0 or 1 or 2, said E is 0 or -CH 2 CH 2 -.

[0063] The specific process is as follows:

[0064]Step 1: Dissolving compound I with an ether solvent, adding alkyllithium dropwise into the solution of compound I at low temperature (-80°C to -20°C) for reaction, while keeping it warm for a period of time (0.5 to 3 hours), Compound II is obtained,

[0065]

[0066] The R is C 0 ~C 5 straight chain alkyl, said n is 0 or 1 or 2, said m is 0 or 1 or 2, said E i...

Embodiment 1

[0077] Preparation of 2,3-difluoro-4-allyl-4′-(trans-4-propylcyclohexyl)-1,1′-biphenyl

[0078] 500ml three-necked bottle, install a thermometer, mechanical stirring, constant pressure dropping funnel, add 31.4g (0.1mol) 2,3-difluoro-4′-(trans-4-propylcyclohexyl)-1,1′- Biphenyl, 188.4g tetrahydrofuran, stirring to cool down to -60°C, dropwise adding 36.5g n-butyllithium, after the dropwise addition, keep warm for 1 hour, add dropwise 11.5g allyl chloride below -50°C, add 0.2g CuCl 2 , -50 ℃ insulation 0.5h, the reaction is complete.

[0079] Add 50g of water dropwise, stir and raise the temperature to 25°C, separate layers, extract the aqueous phase with a small amount of toluene, combine the organic phases, wash with water until neutral, concentrate to obtain 35.4g of crude product, recrystallize 3 times from absolute ethanol to obtain 25.5g of product, yield 72 %, the purity tested by gas chromatography is 99.69%, the melting point mp is 57.6°C, and the clearing point CP is...

Embodiment 2

[0085] Preparation of 2,3-difluoro-4-propyl-4'-(trans-4-pentylcyclohexyl)-1,1'-biphenyl

[0086] According to Example 1, 2,3-difluoro-4'-(trans-4-pentylcyclohexyl)-1,1'-biphenyl and allyl chloride are used as raw materials to obtain 2,3-difluoro- 4-Propyl-4'-(trans-4-pentylcyclohexyl)-1,1'-biphenyl, its purity is 99.9% by gas chromatography, its crystal phase is nearly The crystal phase is 59.4°C, the smectic phase to nematic phase is 88.7°C, and the nematic phase to isotropic phase (clearing point CP) is 123.0°C. The characteristic ion M / Z is tested by mass spectrometry (GC-MS) + for

[0087] 384,355,328,313,273,258,229,203,183,166,151,127,109,81,55.

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
Clear pointaaaaaaaaaa
Login to View More

Abstract

The invention relates to a preparation method of propyl o-fluorobenzene compounds. The preparation method comprises the following steps that lithium reagent is firstly prepared by using a raw material compound I, then coupling reaction occurs between the lithium reagent and allyl chloride or allyl bromide under the catalytic effect of copper, and the obtained product is catalytically hydrogenated to obtain the propyl o-fluorobenzene compounds. The preparation method of propyl o-fluorobenzene compounds provided by the invention has the advantages that the steps are fewer, the yield is high, the method is environmental-friendly, the industrialization is easy to realize, and the problems of more steps, great pollution, fluorine falling and the like in the prior art are solved.

Description

technical field [0001] The invention relates to a preparation method of propyl-o-fluorobenzene compounds, belonging to the technical fields of fine chemical industry and material chemistry. Background technique [0002] In recent years, liquid crystals with negative dielectric anisotropy have been used more and more widely. Ortho-difluorobenzene is an important group of this type of liquid crystal compound. The liquid crystal compound containing this group has low viscosity, high charge retention rate, and superior performance. features. Some of these compounds can be represented by the following structural formula: [0003] [0004] where R is C 0 ~C 5 straight chain alkyl, n is 0 or 1 or 2, m is 0 or 1 or 2, E is 0 or -CH 2 CH 2 -. [0005] GEORGE W.GRAY of John W.Goodby and Merck mentioned similar compounds in J.MATER.CHEM.,1995,5(3),423-430 and Liquid Crystals, 1994,Vol.16,No.4,625-641 respectively The preparation method: [0006] [0007] or the following ...

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): C07C17/354C07C25/18
Inventor 贾公明钟尚宾乔松黄永彤王志勇
Owner VALIANT CO LTD
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com