Method for synthesizing 4-cyclobutyl biphenyl fluorine-containing compound

A technology of cyclobutyl biphenyl and cyclobutenyl biphenyl is applied in the field of synthesis of 4-cyclobutyl biphenyl fluorine-containing compounds, and can solve the problems of high risk factor, high pressure on environmental protection, large amount of waste water and the like, and achieve safety The effect of high performance, less environmental pollution and less operation steps

Active Publication Date: 2018-06-19
山东盛华新材料科技股份有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In the synthetic route 1, the cost of the raw material p-dibromobenzene is high, the selectivity of the lithium substitution reaction is low, and the conversion rate is about 70%. There is a high risk factor in the lithium substitution method with n-BuLi, and the generated waste water contains lithium. Increase the difficulty of three wastes treatment; fluorine-containing phenylboronic acid is not easy to produce, the cost of producing fluorine-containing phenylboronic acid is high, and a large amount of waste water and waste solvents are generated; the cost of purchasing fluorine-containing phenylboronic acid is higher and subject to market constraints; 4-cyclobutenyl Bromobenzene is coupled with fluorine-containing phenylboronic acid and then hydrogenated to obtain the product 4-cyclobutylbiphenyl fluorine-containing compound IX. The yield is low, and it brings health hazards to operators during experiments and production, shortens the life of facilities, and waste liquid More production, greater pressure on environmental protection

Method used

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  • Method for synthesizing 4-cyclobutyl biphenyl fluorine-containing compound
  • Method for synthesizing 4-cyclobutyl biphenyl fluorine-containing compound
  • Method for synthesizing 4-cyclobutyl biphenyl fluorine-containing compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Example 1, a synthesis method of 4-cyclobutylbiphenyl fluorine-containing compound IX, this embodiment is a synthesis method of 4'-cyclobutyl-3,5-difluorobiphenyl, the synthesis route is as follows:

[0018]

[0019]

[0020] Wherein the preparation of 4-cyclobutenyl chlorobenzene V is: under the protection of inert gas, in the 500ml reaction bottle that mechanical stirring, reflux condensation drying tube, feeding funnel are housed, add magnesium sheet 13g, THF35ml successively, stir; To 50°C, add dropwise 20ml of the prepared p-chlorobromobenzene 100g / THF100ml mixed solution into the system, the reaction is initiated, and the temperature is controlled at 50°C to 70°C to add dropwise. A good cyclobutanone 47g / toluene 200ml mixed solution, 90min after the dropwise addition, stop the reaction, pour the reaction solution into a 500ml reaction bottle with 100ml of concentrated hydrochloric acid, stir for 2h, then add 100ml of toluene, stir for 1h and let it stand Sep...

Embodiment 2

[0024] Example 2, a synthesis method of 4-cyclobutylbiphenyl fluorine-containing compound IX. This example is a synthesis method of 4'-cyclobutyl-3,4,5-trifluorobiphenyl. The synthesis route is as follows:

[0025]

[0026]

[0027] Wherein the preparation of 4-cyclobutenyl chlorobenzene V is: under the protection of inert gas, in the 500ml reaction bottle that mechanical stirring, reflux condensation drying tube, feeding funnel are housed, add magnesium sheet 13g, THF35ml successively, stir; To 70°C, add dropwise 20ml of the prepared p-dichlorobenzene 77g / THF100ml mixed solution into the system, the reaction is initiated, and the temperature is controlled at 70°C to 80°C to add dropwise. A good cyclobutanone 47g / toluene 200ml mixed solution, stop the reaction 120min after the dropwise addition, pour the reaction solution into a 500ml reaction bottle with 100ml of concentrated hydrochloric acid, stir for 2h, then add 100ml of toluene, stir for 1h and let it stand Separat...

Embodiment 3

[0031] Embodiment 3, a synthetic method of 4-cyclobutylbiphenyl fluorine-containing compound IX, this embodiment is a synthetic method of 4'-cyclobutyl-3-fluorobiphenyl, the synthetic route is as follows:

[0032]

[0033] Wherein the preparation of 4-cyclobutenyl chlorobenzene V is: under the protection of inert gas, in the 500ml reaction bottle that mechanical stirring, reflux condensation drying tube, feeding funnel are housed, add magnesium sheet 13g, THF35ml successively, stir; To 70°C, add dropwise 20ml of the prepared p-chloroiodobenzene 125g / THF100ml mixed solution into the system, the reaction is initiated, and the temperature is controlled at 40°C to 50°C to add dropwise. A good cyclobutanone 47g / toluene 200ml mixed solution, stop the reaction 120min after the dropwise addition, pour the reaction solution into a 500ml reaction bottle with 100ml of concentrated hydrochloric acid, stir for 2h, then add 100ml of toluene, stir for 1h and let it stand Separate the liqu...

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Abstract

The invention discloses a method for synthesizing a 4-cyclobutyl biphenyl fluorine-containing compound. The method comprises the following steps: by taking chlorine benzene halide as an initial raw material, performing a Grignard reaction; performing a coupling reaction on the chlorine benzene halide with cyclobutanone so as to generate cyclobutanol chlorobenzene; performing a dehydration reactionso as to generate cyclobutene chlorobenzene; performing a one-pot method reaction to generate 4-cyclobutene phenylboronic acid; performing a coupling reaction with fluorine-containing benzene halideso as to generate a 4-cyclobutene biphenyl fluorine-containing compound; performing a hydrogenation reaction, thereby obtaining a 4-cyclobutyl biphenyl fluorine-containing compound IX. The method hasthe characteristics of being high in conversion rate, low in cost, safe and stable in process, short in reaction step, green and environmental-friendly in process route and small in pollutant emission.

Description

technical field [0001] The invention belongs to the technical field of liquid crystal intermediates, and in particular relates to a method for synthesizing 4-cyclobutylbiphenyl fluorine-containing compounds, the structural formula of which is shown in IX: [0002] [0003] Among them: -(F) represents F and H. Background technique [0004] 4-cyclobutylbiphenyl fluorine-containing compound IX is an important intermediate in cyclobutyl-based fluorine-containing liquid crystals, and its synthesis has important application value; Yuan Guoliang et al. introduced the synthesis of 4-cyclobutylbiphenyl Benzene fluorochemical method. [0005] [0006] In the synthetic route 1, the cost of the raw material p-dibromobenzene is high, the selectivity of the lithium substitution reaction is low, and the conversion rate is about 70%. There is a high risk factor in the lithium substitution method with n-BuLi, and the generated waste water contains lithium. Increase the difficulty of ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C17/354C07C25/18
CPCC07C17/263C07C17/35C07C17/354C07C29/40C07F3/02C07F5/025C07C25/18C07C35/50
Inventor 武生喜刘煜阳王德贤杜开昌高跟华
Owner 山东盛华新材料科技股份有限公司
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