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The preparation method of 2-cyano-4'-methylbiphenyl

A technology of methyl biphenyl and p-toluene boronic acid, which is applied in the field of preparation of 2-cyano-4'-methyl biphenyl, can solve the problems of complex catalyst preparation, poor recyclability, and high cost of use, and achieve reaction Mild conditions, high-efficiency catalysis, and environmentally friendly effects

Inactive Publication Date: 2017-04-12
ZHEJIANG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But the used solvent of above-mentioned method is ethanol, and used alkali is potassium carbonate, and the preparation of its catalyst is complicated, and use cost is high, and recyclability is poor, so the application in industry is restricted

Method used

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  • The preparation method of 2-cyano-4'-methylbiphenyl

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Experimental program
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Effect test

Embodiment 1

[0020] Embodiment 1, the preparation method of polystyrene-triphenylphosphine:

[0021] Add 2.0 g (6.9 mmol) of diphenyl (4-vinylphenyl) phosphine, 2.9 ml (27.6 mmol) of styrene, and 3 mL of toluene to a 10 mL three-necked flask, dissolve them, and add 78.0 mg of AIBN (azobisisobutyl Nitrile), N 2 Under protection, stirred and heated to 70°C for 24 hours, TLC detected the disappearance of diphenyl (4-vinylphenyl) phosphine in the reaction solution; concentrated to remove the solvent, dissolved the obtained solid in 6 mL THF (tetrahydrofuran), and added dropwise (about 5 minutes) Added) into 60ml of methanol at 0°C, a white solid was precipitated, filtered with suction to obtain 4.73g of polystyrene-triphenylphosphine compound (III) in the form of white powder, yield: 97%.

Embodiment 2

[0022] Embodiment 2, the preparation method of polystyrene-triphenylphosphine supported palladium catalyst:

[0023] Add 1g of compound (III) and 10ml of THF to a 25ml reaction flask, heat up to 50°C, and then add 84.0mg (0.375mmol) of Pd(OAc) 2 , continue to react at 50°C for 4h, cool to 0°C, add this solution dropwise (about 10 minutes to complete) into 20ml of hexane at 0°C, stir at room temperature for 12h, filter with suction, filter the cake with 5ml of methanol After washing, 1.05 g of black solid polystyrene-triphenylphosphine supported palladium compound was obtained, yield: 97%.

Embodiment 3

[0024] The preparation method of embodiment 3,2-cyano-4'-methylbiphenyl:

[0025] 1.376g (10mmol) of o-chlorobenzonitrile, 1.700g (12.5mmol) of p-tolueneboronic acid and 2.764g (20mmol) of anhydrous sodium carbonate were added to a container containing 100mL EtOH / H 2 In a three-neck flask of O (v / v, 1 / 1), heat to reflux, add 41.4mg of polystyrene-triphenylphosphine supported palladium catalyst, continue to heat and reflux for 1h, TLC detects that the reaction liquid o-chlorobenzonitrile disappears, and suction filter , the filter cake was washed with 3×20ml ethyl acetate, 2×4ml EtOH / H 2 O (v / v, 1 / 1) washing, drying at room temperature to constant weight, reclaiming polystyrene-triphenylphosphine supported palladium catalyst 40.2mg, recovery rate: 97%; the filtrate gained by suction filtration was extracted with 40ml water , the organic phase (at the upper layer) was washed with 20 ml of saturated brine, and the washed organic phase was dried with 2.0 g of anhydrous sodium sul...

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Abstract

The invention discloses a preparation method of 2-cyano-4'-methyl biphenyl. In the existence of a reaction solvent and a catalyst, the Suzuki coupling reaction of chlorobenzonitrile and methylbenzeneboronic acid is performed, the catalyst is polystyrene-triphenylphosphine supported palladium, the reaction solvent is EtOH / H2O, and the volume ratio of EtOH / H2O is (4 to 1) to (1 to 4). The preparation method sequentially comprises the following steps: (1) adding chlorobenzonitrile, methylbenzeneboronic acid and alkali into the reaction solvent, heating until the refluxing, adding the catalyst, and performing the reaction under the refluxing condition; (2) detecting by using TLC in the reaction process, and after the reaction is ended, performing the suction filtration to respectively obtain filtrate and a filter cake; and adding water into the filtrate, washing an obtained organic phase with a saturated saline solution, drying with anhydrous sodium sulfate, and carrying out the column chromatography isolation to obtain 2-cyano-4'-methyl biphenyl.

Description

technical field [0001] The invention belongs to the synthesis process of sartan antihypertensive drug intermediates, and relates to a synthesis method of 2-cyano-4'-methylbiphenyl. Background technique [0002] 2-cyano-4'-methylbiphenyl, also known as sartan biphenyl, English name: 2-Cyano-4'-methylbiphenyl, structural formula: [0003] [0004] 2-cyano-4'-methylbiphenyl is a key intermediate for the preparation of sartan antihypertensive drugs. The general method for synthesizing 2-cyano-4'-methylbiphenyl is o-chlorobenzonitrile and p- Suzuki Coupling Reaction Between Methylboronic Acids. The reaction has the advantages of mild reaction conditions, high yield, and economical and easy-to-obtain raw materials, and is widely used in many fields such as chemical industry, medicine, and pesticide. [0005] Most of the catalytic systems of Suzuki coupling reaction use ligands, most of these ligands are sensitive to air and water, the reaction medium used is highly toxic (suc...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C253/30C07C255/50
CPCC07C253/30C07C255/50
Inventor 章国林郭闪闪赵冬红俞永平
Owner ZHEJIANG UNIV
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