Method for preparing 4'-chloro-2-aminobiphenyl through palladium/carbon catalysis

A technology for catalytic preparation and aminobiphenyl, which is applied in the preparation of amino compounds, chemical instruments and methods, preparation of organic compounds, etc., can solve the problems of high price, difficult to recycle and reuse, and increased reaction cost.

Active Publication Date: 2014-01-29
天津均凯农业科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, since these two catalysts are relatively expensive and require the use of organic phosphine ligands, it is not easy to recycle and reuse after the reaction, which greatly increases the reaction cost.

Method used

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  • Method for preparing 4'-chloro-2-aminobiphenyl through palladium/carbon catalysis
  • Method for preparing 4'-chloro-2-aminobiphenyl through palladium/carbon catalysis
  • Method for preparing 4'-chloro-2-aminobiphenyl through palladium/carbon catalysis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] 0.16g o-chloronitrobenzene, 0.23g p-chlorophenylboronic acid are added in the there-necked flask, add 0.41g potassium phosphate, 0.036g palladium carbon (5% metal content, 69.13% water content), 15mL tetrahydrofuran (molar ratio: o Chloronitrobenzene: p-chlorophenylboronic acid: palladium on carbon: potassium phosphate: tetrahydrofuran = 1:1.5:0.017:1.9:166), heated to 70°C for 12 hours. Stop the reaction, cool down to room temperature, filter with suction, recover the filter cake, evaporate the filtrate to remove the solvent under reduced pressure, add dichloromethane and water to extract the residue, evaporate the solvent to dryness in the organic layer, precipitate a solid, wash with petroleum ether twice, and filter with suction to obtain 4'-Chloro-2-nitrobiphenyl, yield 24.32%. The reaction structure is as follows:

[0033]

Embodiment 2

[0035] 0.16g o-chloronitrobenzene, 0.23g p-chlorophenylboronic acid joins in the there-necked flask, add 0.41g potassium carbonate, 0.036g palladium charcoal, 15mL toluene (the molar ratio is: o-chloronitrobenzene: p-chlorophenylboronic acid: palladium Carbon: Potassium Carbonate: Toluene=1:1.5:0.017:3:130), the temperature was raised to 100°C for 12h. Stop the reaction, cool down to room temperature, filter with suction, recover the filter cake, evaporate the filtrate to remove the solvent under reduced pressure, add dichloromethane and water to extract the residue, evaporate the solvent to dryness in the organic layer, precipitate a solid, wash with petroleum ether twice, and filter with suction to obtain 4'-Chloro-2-nitrobiphenyl, yield 34.51%.

Embodiment 3

[0037] 0.16g o-chloronitrobenzene, 0.23g p-chlorophenylboronic acid joins in the there-necked flask, adds 0.41g potassium carbonate, 0.020g palladium carbon (molar ratio is: o-chloronitrobenzene: p-chlorophenylboronic acid: palladium carbon: carbonic acid Potassium=1:1.5:0.009:3), 15g of DMAC and 1g of water (weight ratio: water:DMAC=1:15) were heated to 130°C for 12h. Stop the reaction, cool down to room temperature, filter with suction, recover the filter cake, evaporate the filtrate to remove the solvent under reduced pressure, add dichloromethane and water to extract the residue, evaporate the solvent to dryness in the organic layer, precipitate a solid, wash with petroleum ether twice, and filter with suction to obtain 4'-Chloro-2-nitrobiphenyl, yield 34.16%.

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Abstract

The invention relates to a method for preparing 4'-chloro-2-aminobiphenyl through palladium/carbon catalysis. The method comprises the steps: reacting in a solvent under a heating condition by taking p-chlorophenylboronic acid and o-chloronitrobenzene as raw materials, palladium/carbon as a catalyst and a weak base as a catalyst promoter to generate 4'-chloro-2-nitrobiphenyl; reducing 4'-chloro-2-nitrobiphenyl in a polar solvent by using a reducing agent zinc or iron powder under the heating condition to obtain 4'-chloro-2-aminobiphenyl. The invention finds a method which is lower in cost, simpler and more convenient to operate and environment-friendly through screening and researching yield influencing factors such as catalyst dosage, reaction solvent proportion, reaction temperature, reaction time, palladium/carbon recovered and reused times and the like in palladium/carbon catalytic coupling reaction.

Description

technical field [0001] The invention relates to a method for preparing 4'-chloro-2-aminobiphenyl catalyzed by palladium carbon. Background technique [0002] Intermediate: 4'-Chloro-2-aminobiphenyl [0003] English name: 4'-chloro-2–aminobiphenyl [0004] Molecular formula: C 12 h 10 ClN [0005] Molecular weight: 203.50 [0006] The structural formula is shown in the figure below: [0007] [0008] Transition metal-catalyzed cross-coupling reactions are an important method for the preparation of biphenyls. Commonly used metal catalysts include palladium, nickel, ruthenium, manganese, etc., among which palladium compounds are the most commonly used, and palladium chloride and palladium acetate are the most common. However, since these two catalysts are relatively expensive and require the use of organic phosphine ligands, it is not easy to recycle and reuse after the reaction, which greatly increases the reaction cost. The invention utilizes palladium charcoal to ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/52C07C209/36
CPCY02P20/584
Inventor 尚振华栗晓东
Owner 天津均凯农业科技有限公司
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