A method for synthesizing biaryls

A technology for biaryls and halogenated aromatics, which is applied in the field of organic catalytic synthesis, can solve the problems of environmental pollution, high reaction cost, and difficulty in large-scale production, and achieve the effects of low corrosion, low dosage, and easy preparation

Active Publication Date: 2018-12-11
YANGZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The purpose of the present invention is to provide a method for synthesizing biaryls to solve the problems of high reaction cost, environmental pollution and difficulty in large-scale production in the prior art

Method used

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  • A method for synthesizing biaryls

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0012] 1. Prepare the catalyst:

[0013] Weigh 1231.6 mg (10 mol) of p-methoxyaniline and dissolve it in 100 ml of aqueous hydrochloric acid with a concentration of 1 mol / L to obtain solution a.

[0014] Weigh 44.3 mg of palladium dichloride and dissolve in 100 ml of aqueous hydrochloric acid with a concentration of 1 mol / L to obtain solution b.

[0015] Add solution b to solution a, stir for 2 minutes after mixing, and let stand for 24 hours. Adjust the pH value to 7.0 with 1mol / L sodium hydroxide aqueous solution to obtain a flocculent precipitate, which is centrifuged, washed three times with deionized water, and dried at 100°C for 6 hours to obtain a blue-yellow solid, that is, poly-p-methoxyaniline-loaded nanoparticles palladium.

[0016] 2. Synthesis of biaryls:

[0017] In a 50 ml reaction tube, add 6 mg poly-p-methoxyaniline supported nano-palladium catalyst, 2.04 g (10 mmol) iodobenzene, 589 mg (10 mmol) hydrazine hydrate (85%), 1.29 g (10 mmol) diiso Propylethyla...

Embodiment 2

[0019] Other conditions are the same as in Example 1, and the influence of the reaction temperature on the reaction is checked, and the experimental results are as shown in Table 1.

[0020] Table 1 Effect of reaction temperature

[0021] Reaction temperature (°C)

[0022] It can be seen from the above table that the effect is the best and the yield is the highest when the reaction temperature is 140°C.

Embodiment 3

[0024] Other conditions are the same as in Example 1, and the influence of the consumption of the reducing agent hydrazine hydrate on the reaction is checked, and the experimental results are shown in Table 2.

[0025] Table 2 The effect of reducing agent hydrazine hydrate dosage

[0026] Hydrazine hydrate / mmol

[0027] It can be seen from the above table that the yield is the highest when the molar ratio of reducing agent hydrazine hydrate to iodobenzene is 1:1.

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Abstract

The invention discloses a method for synthesizing biaryl hydrocarbons, which belongs to the field of organic catalytic synthesis. Using poly-p-methoxyaniline-loaded nano-palladium as a catalyst and diisopropylethylamine as a base in N-methylpyrrolidone solvent, hydrazine hydrate is used to catalyze the reduction of halogenated hydrocarbons to prepare biaryls. The reaction conditions of the present invention are mild, the product is easy to separate, the reaction is easy to operate, and has good safety; secondly, the catalyst used in the method is easy to prepare, the amount is small, and the catalyst can be recycled many times after the reaction; in addition, the present invention uses Green alkali and reducing agent, less solid waste, low corrosion, green and environmentally friendly.

Description

technical field [0001] The invention belongs to the field of organic catalytic synthesis. Background technique [0002] Biaryls are an important class of organic compounds, which widely exist in natural products, medicines, dyes, functional polymers, organic conductors and semiconductors. In 1901, German chemist Ullmann discovered that aryl halides could be used to prepare symmetrical biaryls under the catalysis of active copper powder. However, the reaction conditions were very harsh and required high temperatures (generally greater than 200 o C), and use excessive copper catalysis, although it has been improved by people in various experiments, it also faces many problems, such as large amount of catalyst, difficult to recycle, complex reducing agent, etc., which makes the reaction cost high And pollute the environment, not suitable for large-scale production. Contents of the invention [0003] The purpose of the present invention is to provide a method for synthesizin...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C1/26C07C15/14
CPCY02P20/584
Inventor 俞磊刘永红唐大亮刘名轩
Owner YANGZHOU UNIV
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