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A kind of synthetic method of 4-cyclopropyl biphenyl fluorine-containing compound

A technology of cyclopropyl biphenyl and cyclopropenyl biphenyl, which is applied in the field of synthesis of 4-cyclopropyl biphenyl fluorine-containing compounds, can solve the problems of high environmental protection pressure, low product yield, shortened facility life and the like, and achieves Less solvent usage, high safety performance and less environmental pollution

Active Publication Date: 2021-04-13
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

[0004] 4-Cyclopropylbiphenyl fluorine-containing compound IX is an important intermediate in cyclopropyl-based fluorine-containing liquid crystals, and its synthesis has important application value. At present, there is no relevant literature report on the synthesis of this product; Yuan, Guoliang; Liang, People such as Zhian introduced the method for synthesizing target product 4-cyclopentyl biphenyl fluorine-containing compound as synthetic route 1
The process of synthetic route 1 has the following disadvantages: the raw material cost of p-dibromobenzene is high, the selectivity of the lithiation reaction is low, and the conversion rate is about 70%. Difficulty; fluorine-containing phenylboronic acid is not easy to prepare, and the preparation cost is high, and a large amount of waste water and waste solvents are generated during the preparation process; the cost of purchasing fluorine-containing phenylboronic acid is higher and subject to market constraints; 4-cyclopentenylbromobenzene and fluorine-containing The product 4-cyclopentylbiphenyl fluorine-containing compound IX is obtained by hydrogenation after coupling of phenylboronic acid. The product yield is low, and it brings health hazards to operators during experiments and production, shortens the life of facilities, and generates more waste liquid. Environmental pressure is high

Method used

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  • A kind of synthetic method of 4-cyclopropyl biphenyl fluorine-containing compound
  • A kind of synthetic method of 4-cyclopropyl biphenyl fluorine-containing compound
  • A kind of synthetic method of 4-cyclopropyl biphenyl fluorine-containing compound

Examples

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Embodiment 1

[0019] Example 1, a synthesis method of 4-cyclopropylbiphenyl fluorine-containing compound IX. This example is specifically a synthesis method of 4'-cyclopropyl-3,5-difluorobiphenyl. The synthesis route is as follows:

[0020]

[0021] Wherein the preparation of 4-cyclopropenyl 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 successively, THF35ml, stir; Be warming up to 50°C, add dropwise 20ml of the prepared p-chlorobromobenzene 100g / THF100ml mixed solution into the system, the reaction is triggered, and the temperature is controlled at 50°C-70°C to add dropwise. Cyclopropanone 35g / toluene 200ml mixed solution, stop the reaction 90min after the dropwise addition, pour the reaction solution into a 500ml reaction bottle with 100ml of concentrated hydrochloric acid, stir for 2h, then add toluene 100ml, stir for 1h and let it stand fo...

Embodiment 2

[0025] Example 2, a synthesis method of 4-cyclopropylbiphenyl fluorine-containing compound IX, this example is a synthesis method of 4'-cyclopropyl-3,4,5-trifluorobiphenyl, the synthesis route is as follows:

[0026]

[0027] Wherein the preparation of 4-cyclopropenyl 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 successively, THF35ml, stir; Be warming up to 70°C, drop 20ml of the prepared p-dichlorobenzene 70g / THF100ml mixed solution into the system, the reaction is triggered, and the temperature is controlled at 70°C to 80°C to add dropwise. Cyclopropanone 35g / 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 toluene 100ml, stir for 1h and let it stand for liquid separatio...

Embodiment 3

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

[0032]

[0033] Wherein the preparation of 4-cyclopropenylchlorobenzene V is: under the protection of inert gas, in the 500ml reaction bottle that mechanical stirring, reflux condensation drying tube are housed, add magnesium sheet 13g, THF35ml successively, stir; Be warming up to 70 ℃, Add dropwise 20ml of the prepared p-chloroiodobenzene 115g / THF100ml mixed solution into the system, the reaction is initiated, and the temperature is controlled at 40°C to 50°C to add dropwise. 35g / 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 toluene 100ml, stir for 1h and let the liquid separate, the organic phase Reserve...

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Abstract

The invention discloses a method for synthesizing 4-cyclopropylbiphenyl fluorine-containing compounds. Using p-chlorohalobenzene as an initial raw material, the Grignard reagent of p-chlorohalobenzene is generated by Grignard reaction; Propanol chlorobenzene; dehydration reaction to generate cyclopropenyl chlorobenzene; one-pot reaction to generate 4‑cyclopropenylphenylboronic acid; coupling reaction with fluorine-containing halobenzene to generate 4‑cyclopropenylbiphenyl fluorinated compound; hydrogenation The reaction gives 4-cyclopropyl biphenyl fluorine-containing compound. The invention has the characteristics of high conversion rate, low cost, safe and stable process, short reaction steps, high yield, green process route and less pollutant discharge.

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-cyclopropylbiphenyl 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-Cyclopropylbiphenyl fluorine-containing compound IX is an important intermediate in cyclopropyl-based fluorine-containing liquid crystals, and its synthesis has important application value. At present, there is no relevant literature report on the synthesis of this product; Yuan, Guoliang; Liang, Zhian et al. introduced a method for synthesizing the target product 4-cyclopentylbiphenyl fluorine-containing compound as shown in Synthesis Route 1. [0005] [0006] Synthetic route 1 [0007] In the synthetic route 1, the target product synthesized is 4-cyclopentyl biphenyl fluorine-containing compound. The process of synthetic rout...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C17/263C07C17/35C07C17/354C07C29/40C07F5/02C07C25/18C07C25/24C07C35/50
CPCC07C17/263C07C17/35C07C17/354C07C29/40C07F5/025C07C25/18C07C25/24C07C35/50
Inventor 武生喜刘煜阳王德贤纪显光程秀红
Owner 山东盛华新材料科技股份有限公司