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Process for catalytic synthesis of 2-cyano-4'-methyl biphenyl

A methyl biphenyl and process technology, applied in the field of catalytic synthesis of 2-cyano-4'-methyl biphenyl, can solve the problem of large amount of metal palladium and the like, achieve easy recovery and reuse, simple reaction conditions and high activity Effect

Active Publication Date: 2021-04-16
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The literature (Qi Liang, Wen Yong-ju, Lv Mei-yun. Study on the synthesis of sartanbiphenyl[J]. Chemical Research And Application, 2015, 1:1004-1656) also uses a one-pot method to prepare 2-cyano-4' -Methyl biphenyl, but its metallic palladium consumption is big (2% of substrate o-chlorobenzonitrile), when temperature 80 ℃, yield is 64%; When temperature 120 ℃, yield drops to 45%, and document Preparation of 2-cyano-4' -Methyl biphenyl can be recovered, the temperature is 150°C, and the yield is 98%. The disadvantage is that compared with the present invention, a higher temperature is required

Method used

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  • Process for catalytic synthesis of 2-cyano-4'-methyl biphenyl
  • Process for catalytic synthesis of 2-cyano-4'-methyl biphenyl
  • Process for catalytic synthesis of 2-cyano-4'-methyl biphenyl

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Add 2-(di-tert-butylphosphine)biphenyl and triphenylbenzene 1:1 (2-(di-tert-butylphosphine)biphenyl dosage 100mg) into the reactor, then add 2g dimethoxymethane and 1g of phosphotungstic acid was quickly flushed into nitrogen, and reacted at 150°C for 8 hours to obtain a phosphorus-containing palladium catalyst support, which was used to prepare 2-cyano-4'-methylbiphenyl from o-chlorobenzonitrile.

[0020] In the pressure tube, add 137.5mg (1mmoL) of o-chlorobenzonitrile, and 163.1mg (1.2mmoL) of p-tolueneboronic acid and 2 equivalents of CSCO 3 , 100 mg containing 2-(di-tert-butylphosphine) biphenyl polymer carrier and palladium acetate (1%) and solvent dioxane 2 mL. Fill the pressure tube with argon gas and tighten the pressure tube, put it in an oil bath at 130°C for 5 hours, after the reaction, take out the pressure tube and cool it down to room temperature, take a sample, and check the conversion rate and selectivity by gas chromatography. The reaction results are ...

Embodiment 2

[0024] Add XPhos and triphenylbenzene 1:2 (the dosage of XPhos is 100mg) into the reaction kettle, then add 3g of dimethoxymethane and 2g of phosphotungstic acid, quickly flush with argon, react at 170°C for 10h, and get Phosphine-containing palladium catalyst support for the preparation of 2-cyano-4'-methylbiphenyl from o-chlorobenzonitrile.

[0025] In the pressure tube, add 137.5mg (1mmoL) of o-chlorobenzonitrile, and 163.1mg (1.2mmoL) of p-tolueneboronic acid and 2 equivalents of CSCO 3 , 100 mg containing XPhos polymer carrier and palladium acetate (1%) and solvent dioxane 2 mL. Fill the pressure tube with nitrogen and tighten it, put it in an oil bath at 130°C and react for 10 hours. After the reaction, take out the pressure tube and cool it down to room temperature, take a sample, and use gas chromatography to detect the conversion rate and selectivity. The reaction results are shown in Table 1. As shown in Example 2;

[0026]

[0027] Preparation of 2-cyano-4'-met...

Embodiment 3

[0029] Add XantPhos and triphenylbenzene 1:3 (XantPhos dosage 100mg) into the reaction kettle, then add 4g of dimethoxymethane and 3g of phosphotungstic acid, quickly flush with argon, react at 180°C for 15h, and get Phosphine-containing palladium catalyst support for the preparation of 2-cyano-4'-methylbiphenyl from o-chlorobenzonitrile.

[0030] In the pressure tube, add 137.5mg (1mmoL) of o-chlorobenzonitrile, and 163.1mg (1.2mmoL) of p-tolueneboronic acid and 2 equivalents of CSCO 3 , 100 mg containing XantPhos polymer carrier and palladium acetate (1%) and solvent dioxane 2 mL. Fill the pressure tube with argon gas and tighten the pressure tube, put it in an oil bath at 130°C for 15 hours. After the reaction, take out the pressure tube and cool it down to room temperature, take a sample, and use gas chromatography to detect the conversion rate and selectivity. The reaction results are shown in Table 1. Shown in embodiment 3;

[0031]

[0032] Preparation of 2-cyano-4...

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Abstract

The invention relates to a method for catalytic synthesis of 2-cyano-4'-methyl biphenyl. The process comprises the following steps: firstly, preparing a phosphine-containing material carrier: putting a phosphine ligand, triphenyl benzene and dimethoxy methane into a reaction kettle in proportion, then adding phosphotungstic acid, and preparing a phosphine-containing polymer carrier at a high temperature under protective gas; then, performing catalytic synthesis to obtain 2-cyano-4'-methyl biphenyl: adding a carrier, metal palladium and an o-chloro benzonitrile substrate, adding p-toluene boronic acid, adding a solvent, adding alkali, and obtaining 2-cyano-4'-methyl biphenyl at medium-high temperature and under reaction pressure. The method has the advantages that the catalyst can be recycled and has higher activity and selectivity and good stability, the loss of metal palladium is prevented, and the method is suitable for industrial production.

Description

technical field [0001] The invention relates to a process for catalytically synthesizing 2-cyano-4'-methylbiphenyl, in particular to a process for preparing 2-cyano-4'-methylbiphenyl by catalyzing o-chlorobenzonitrile. Background technique [0002] 2-cyano-4'-methylbiphenyl belongs to aromatic compounds and is a pharmaceutical intermediate, which can be used to synthesize new sartan antihypertensive drugs, such as losartan, valsartan, iprosartan, ibe Shatan et al. [0003] The literature (Qi Liang, Wen Yong-ju, Lv Mei-yun. Study on the synthesis of sartanbiphenyl[J]. Chemical Research And Application, 2015, 1:1004-1656) also uses a one-pot method to prepare 2-cyano-4' -Methyl biphenyl, but its metallic palladium consumption is big (2% of substrate o-chlorobenzonitrile), when temperature 80 ℃, yield is 64%; When temperature 120 ℃, yield drops to 45%, and document Preparation of 2-cyano-4' -Methyl biphenyl can be recovered, the temperature is 150° C., and the yield is 98%. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/50C07C253/30B01J31/24
CPCY02P20/584
Inventor 黄军吴明伟
Owner NANJING UNIV OF TECH
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