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Method for preparing biaryl compound in pure water

A technology of compound and pure aqueous solution, which is applied in the field of preparing biaryl compounds, to achieve the effects of solving reaction difficulties, wide application prospects, and simplifying the operation process

Inactive Publication Date: 2014-06-25
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, the preparation of biaryl compounds by using polyethylene glycol-modified N-heterocyclic carbene in pure aqueous phase Suzuki reaction has not been reported

Method used

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  • Method for preparing biaryl compound in pure water

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] The preparation of embodiment 1 4-phenyl anisole

[0016] First, palladium chloride (0.0025mmol), imidazolium salt I (0.01mmol), 4-bromoanisole (0.5mmol), phenylboronic acid (0.75mmol), triethylamine (1.0mmol) and water (1mL) were added successively. into a round-bottomed flask and react for 10 minutes at 100°C with magnetic stirring. After the reaction was completed, 15 mL of saturated brine was added to quench the reaction, and the reaction mixture was extracted with ethyl acetate (15 mL×3). The eluent used for analysis is petroleum ether, and the product structure is passed through 1 H NMR and mass spectral identification. The separation yield reached 97%.

Embodiment 2

[0017] The preparation of embodiment 2 4-phenylnitrobenzene

[0018] First, palladium acetate (0.0025mmol), imidazolium salt II (0.01mmol), 4-bromonitrobenzene (0.5mmol), phenylboronic acid (0.75mmol), triethylamine (1.0mmol) and water (1mL) were added to In a round bottom flask, react under magnetic stirring at 100°C for 10 minutes. After the reaction was completed, 15 mL of saturated brine was added to quench the reaction, and the reaction mixture was extracted with ethyl acetate (15 mL×3). The eluent used for analysis is petroleum ether, and the product structure is passed through 1 H NMR and mass spectral identification. The separation yield reached 96%.

Embodiment 3

[0019] The preparation of embodiment 3 4-phenylacetophenone

[0020] First, palladium chloride (0.0025mmol), imidazolium salt III (0.01mmol), 4-bromoacetophenone (0.5mmol), phenylboronic acid (0.75mmol), triethylamine (1.0mmol) and water (1mL) were added in sequence. into a round bottom flask and react for 5 minutes at 100°C with magnetic stirring. After the reaction was completed, 15 mL of saturated brine was added to quench the reaction, and the reaction mixture was extracted with ethyl acetate (15 mL×3). The eluent used for analysis is petroleum ether, and the product structure is passed through 1 H NMR and mass spectral identification. The separation yield reaches 95%.

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Abstract

The invention discloses a method for preparing a biaryl compound in a pure water solution, which belongs to the technical field catalytic chemistry. The method is a method for preparing a biaryl compound by undergoing a Suzuki cross-coupling reaction on an aryl halide and aryl boronic acid. The method comprises the following steps of: adding an aryl halide, arylboronic acid, an alkali, a catalyst and a methoxy end-capped and polyethylene glycol-modified imidazole salt in the molar ratio of 0.5:0.75:1.0:(0.0025-0.005):0.01-0.02 into 1 mL of water; reacting at the temperature of 100 DEG C for 5-480 minutes; after reacting, adding 15mL of saturated saline solution for undergoing a quenching reaction; extracting a reaction product from a reaction mixture with 15 mL of acetic ether for three times; combining organic phases; concentrating a filtrate; and separating with column chromatography to obtain an analytically pure biaryl compound. The method has the characteristics that: the reaction is undergone in pure water serving as an environmentally-friendly solvent without adding any organic solvent; the problem of difficulty in reacting a water-soluble substrate in a pure water system is solved; and inert gas protection is not required in a reaction process, operation is easy, and industrial production is easy.

Description

technical field [0001] The invention relates to a method for preparing biaryl compounds in pure aqueous solution, which belongs to the technical field of organic compound catalytic chemistry. Background technique [0002] Biaryl compounds widely exist in natural products, medicine and various organic functional materials (Chem.Rev.2002,102,1359; Chem.Rev.2004,104,2127; J.Am.Chem.Soc.2006,128 ,16641). Palladium-catalyzed Suzuki cross-coupling reactions are the building blocks for C sp2 -C sp2 One of the most effective methods of bonding (Chem.Rev.1995,95,2457). Suzuki reactions in aqueous phase are generally only applicable to water-soluble substrates. For non-water-soluble substrates, the problem that the reaction rate is limited by the water solubility of the substrate is generally solved by adding organic co-solvents, surfactants, microwave heating, etc. (Chem.Rev.2009,109,725; J.Org.Chem.2011 , 76, 4379; Chem. Commun. 2005, 2881). However, the above method not only ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07B37/00C07C43/205C07C41/30C07C205/06C07C201/12C07C49/784C07C45/68C07C255/50C07C253/30C07C255/54C07C39/15C07C37/11C07C51/353C07C63/331C07D213/16C07D213/64C08G65/48
Inventor 刘春刘宁金子林
Owner DALIAN UNIV OF TECH
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