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Method for preparing 2-dicyclohexylphosphine-2,4,6-di-iso-propylbiphenyl

A technology of triisopropylbiphenyl and dicyclohexylphosphine, applied in the field of preparing 2-dicyclohexylphosphine-2,4,6-triisopropylbiphenyl, which can solve the problem of affecting product purity and quality, and scale-up production Inconvenient operation, troublesome post-processing and other problems, to achieve the effect of ensuring purity and quality, high yield, and simple post-processing

Active Publication Date: 2016-01-27
PANJIN GELIN KAIMO TECH CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] But the disadvantage of this method is that the yield is not high, only 80%; the second is that the catalyst cuprous chloride is used in the reaction with dicyclohexylphosphine chloride, and as a result, it is necessary to use ammonia water for multiple washings in the post-treatment of the product Cuprous chloride can be removed completely, otherwise it will affect the purity and quality of the product, so the post-processing is troublesome, which is extremely inconvenient for the enlarged production operation

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  • Method for preparing 2-dicyclohexylphosphine-2,4,6-di-iso-propylbiphenyl
  • Method for preparing 2-dicyclohexylphosphine-2,4,6-di-iso-propylbiphenyl
  • Method for preparing 2-dicyclohexylphosphine-2,4,6-di-iso-propylbiphenyl

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preparation example Construction

[0036] The invention provides a preparation method of 2-dicyclohexylphosphine-2,4,6-triisopropylbiphenyl shown in formula (I), comprising:

[0037] Under the protection of an inert gas such as nitrogen, add butyllithium dropwise to 2-halo-2,4,6-triisopropylbiphenyl represented by formula (II) at -10-10°C, and react for 0.5-3 Hours, then drop dicyclohexylphosphine chloride at -10-10°C, naturally rise to room temperature and react for 1-5 hours, add saturated aqueous solution of weak acid and weak base salt to the reaction liquid in an ice-water bath to quench the reaction, and separate , The organic phase was precipitated, the solvent was removed, crystallized by adding alcohol, and filtered to obtain white 2-dicyclohexylphosphine-2,4,6-triisopropylbiphenyl.

[0038] Among them, 2-halo-2,4,6-triisopropylbiphenyl is 2-chloro-2,4,6-triisopropylbiphenyl or 2-bromo-2,4,6-triisopropyl biphenyl. Butyllithium may be n-butyllithium, sec-butyllithium or tert-butyllithium, preferably n...

Embodiment 1

[0058] Under nitrogen protection, add 200mL of THF and 31g of 2,4,6-triisopropylbromobenzene into a 1L three-necked flask, drop to 0°C, add 46mL of 2.5M n-butyllithium dropwise, and react for 1 hour , 20g of o-chlorobromobenzene was added dropwise at 0°C, and the reaction was completed for 1 hour to generate 2-chloro-2,4,6-triisopropylbiphenyl;

[0059] Add 42mL of 2.5M n-butyllithium dropwise to the reaction solution at 0°C. After the dropwise reaction is completed for 1 hour, 26.7g of dicyclohexylphosphine chloride is added dropwise, and the reaction is naturally raised to room temperature for 2 hours. Add 200 mL of saturated ammonium chloride aqueous solution dropwise to the reaction liquid in an ice-water bath to quench, separate the liquid, desolventize the organic phase, add methanol to crystallize, and filter to obtain white 2-dicyclohexylphosphine-2,4,6-triiso Propyl biphenyl 45g, yield 90%.

[0060] figure 1 and figure 2 are the prepared 2-dicyclohexylphosphine-2,...

Embodiment 2

[0065] Under nitrogen protection, add 200mL of anhydrous methyl tetrahydrofuran and 28g of 2,4,6-triisopropylbromobenzene to a 1L three-necked flask, drop to -10°C, add 1.0M sec-butyllithium 156mL dropwise, After the dropwise reaction for 30 minutes, 20 g of o-chlorobromobenzene was added dropwise at 10°C, and the reaction was completed for 20 minutes to generate 2-chloro-2,4,6-triisopropylbiphenyl;

[0066] 42mL of 2.5M sec-butyllithium was added dropwise to the reaction solution at -10°C, the dropwise reaction was completed for 1 hour, 26.7g of dicyclohexylphosphine chloride was added dropwise, and the reaction was allowed to rise naturally to room temperature for 3 hours. Add 200 mL of saturated ammonium chloride aqueous solution dropwise to the reaction liquid in an ice-water bath to quench, separate the liquid, desolventize the organic phase, add methanol to crystallize, and filter to obtain white 2-dicyclohexylphosphine-2,4,6-triiso Propyl biphenyl 42g, yield 88%.

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Abstract

The invention discloses a method for preparing 2-dicyclohexylphosphine-2,4,6-di-iso-propylbiphenyl. The method comprises the following steps of performing low-temperature lithiation on 2-halogen-2,4,6-di-iso-propylbiphenyl, and reacting the lithiated 2-halogen-2,4,6-di-iso-propylbiphenyl with dicyclohexylchlorophosphine. The method disclosed by the invention has the advantages of high yield, simplicity in aftertreatment and easiness in operation. An optimized implementation scheme according to the method disclosed by the invention comprises the following steps of taking 2,4,6-triisopropyl halo-benzene as an initial raw material, performing low-temperature lithiation, and reacting with o-dihalo-benzene to obtain the 2-halogen-2,4,6-di-iso-propylbiphenyl; continuously performing the low-temperature lithiation, and reacting with the dicyclohexylchlorophosphine so as to prepare the 2-dicyclohexylphosphine-2,4,6-di-iso-propylbiphenyl. The method disclosed by the invention has the advantages that the raw material is easily obtained, the operation is simple, products with high yield and high purity can be obtained, and the method is especially suitable for large-scale industrialized production.

Description

technical field [0001] The invention relates to a method for preparing 2-dicyclohexylphosphine-2,4,6-triisopropylbiphenyl, which belongs to the technical field of organic synthesis. Background technique [0002] 2-Dicyclohexylphosphine-2,4,6-triisopropylbiphenyl plays an important role in modern organic synthesis and practical applications. It is mainly used as a catalyst in coupling reactions such as Suzuki, Heck, and Negishi. It is widely used in the synthesis of liquid crystal materials, photofunctional complexes and other substances. [0003] The existing method for preparing 2-dicyclohexylphosphine-2,4,6-triisopropylbiphenyl is to make Grignard reagent with 2,4,6-triisopropylbromobenzene and magnesium chips, and O-chlorobromobenzene is combined, and then combined with dicyclohexylphosphine chloride under the action of catalyst cuprous chloride, after quenching the reaction, the organic phase is washed to anhydrous with ammonia water, that is, the catalyst cuprous chlor...

Claims

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Application Information

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IPC IPC(8): C07F9/50
Inventor 饶志华宫宁瑞
Owner PANJIN GELIN KAIMO TECH CO LTD
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