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Synthetic process of phosphorus ligand type compound

A synthesis process and compound technology, which is applied in the field of synthesis process of phosphorus ligand compounds, can solve the problems of low yield and cumbersome synthesis operation, and achieve the effect of simple operation process and significant application value

Active Publication Date: 2015-04-01
上海泰坦科技股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In order to overcome the complex operation of phosphorus ligand compounds such as (3-bromopropyl) triphenylphosphonium bromide and (1-propyl) triphenylphosphorus bromide in the prior art, and the low yield Technical problem, after the present inventor has carried out a large amount of in-depth studies, thus has completed the present invention

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] This embodiment relates to a synthesis process of phosphorus ligand compounds, comprising the following steps:

[0017] Step 1, dissolve 1-bromopropane and triphenylphosphine in dichloromethane according to equimolar numbers (both 1 mole), stir evenly, then add acetic acid to adjust and maintain the pH value of the reaction system at 1.7, and then heat up Reflux reaction at 35°C for 16 hours, and then adjust the pH of the reaction system to 3.5 with sodium hydride;

[0018] Step 2, cooling to 5°C, and after the crystallization is complete, filter to obtain a filter cake;

[0019] Step 3: wash the filter cake with dichloromethane, and vacuum dry to obtain 362.8 g of off-white solid, which is (1-propyl)triphenylphosphine bromide, with a HPLC purity of 99.4% and a yield of 93.6%.

[0020] 1 H-NMR (CDCl 3 , 500MHz) δ: 0.87(t, CH 3 ), 1.65 (m, CH 2 ), 3.74(t,CH 2 -P + ), 7.74 (s, benzene ring hydrogen).

Embodiment 2

[0022] This embodiment relates to a synthesis process of phosphorus ligand compounds, comprising the following steps:

[0023] Step 1, dissolve 1-bromopropane and triphenylphosphine in dichloromethane according to equimolar numbers (both 1 mole), stir evenly, then add acetic acid to adjust and maintain the pH value of the reaction system at 1.2, and then heat up Carry out reflux reaction at 38°C for 20h, and then adjust the pH value of the reaction system to 3.8 with sodium hydride;

[0024] Step 2, cooling to 1°C, and after the crystallization is complete, filter to obtain a filter cake;

[0025] Step 3: wash the filter cake with dichloromethane, and vacuum dry to obtain 358.9 g of off-white solid, which is (1-propyl)triphenylphosphine bromide, with a HPLC purity of 99.2% and a yield of 92.4%.

[0026] 1 H-NMR (CDCl 3 , 500MHz) δ: 0.88(t, CH 3 ), 1.64 (m, CH 2 ), 3.75(t,CH 2 -P + ), 7.76 (s, benzene ring hydrogen).

Embodiment 3

[0028] This embodiment relates to a synthesis process of phosphorus ligand compounds, comprising the following steps:

[0029] Step 1, dissolve 1-bromopropane and triphenylphosphine in dichloromethane according to equimolar numbers (both 1 mole), stir evenly, then add acetic acid to adjust and maintain the pH value of the reaction system at 2.0, and then heat up Carry out reflux reaction at 40°C for 13h, and then adjust the pH value of the reaction system to 3.2 with sodium hydride;

[0030] Step 2, cooling to 3°C, and after the crystallization is complete, filter to obtain a filter cake;

[0031] Step 3: wash the filter cake with dichloromethane, and vacuum dry to obtain 356.1 g of off-white solid, which is (1-propyl)triphenylphosphine bromide, with a HPLC purity of 99.1% and a yield of 91.6%.

[0032] 1 H-NMR (CDCl 3 , 500MHz) δ: 0.87(t, CH 3 ), 1.66 (m, CH 2 ), 3.73(t,CH 2 -P + ), 7.73 (s, benzene ring hydrogen).

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Abstract

The invention relates to a synthetic process of a phosphorus ligand type compound. The synthetic process comprises the following steps: 1, dissolving 1-bromopropane and triphenylphosphine in dichloromethane, stirring uniformly, then adding organic acid to adjust the pH value, maintaining the pH value of the reaction system between 1.2 and 2.0, heating to perform reflux reaction, and then adjusting the pH value of the reaction system to be 3.2-3.8 by using sodium hydride; 2, cooling, crystallizing and filtering to obtain a filter cake; and 3, washing the filter cake by adopting dichloromethane, and performing vacuum drying to obtain an off-white solid namely (1-propyl) triphenyl phosphorus bromide. The process provided by the invention can be performed smoothly without nitrogen protection, so that the operation process of synthesis is simpler and the yield can reach over 90%; and the process is also suitable for synthesizing (3-bromopropyl) triphenyl phosphorus bromide by adopting 1,3-bromopropane and triphenyl phosphorus bromide, is very suitable for industrial large-scale application, and has significant application values.

Description

technical field [0001] The invention relates to a synthesis process of a ligand compound, in particular to a synthesis process of a phosphorus ligand compound. Background technique [0002] Phosphorus ligand compounds refer to compounds containing C-P bonds or phosphoric acid derivatives containing organic groups. Phosphorus ligand compounds and catalysts are currently widely used in palladium-catalyzed cross-coupling reactions. Pd-catalyzed coupling reactions have relatively Many types, currently the most widely used are Suzuki reaction, Stille reaction, Heck reaction, Buchwald reaction, Sonogashira reaction, asymmetric catalytic reaction, etc. Therefore, in-depth research on phosphorus ligand compounds such as (3-bromopropyl)triphenyl The synthesis technology of phenylphosphorus bromide and (1-propyl)triphenylphosphorus bromide has remarkable application value. [0003] CN101445518A (published on June 3, 2009) discloses a preparation method of phosphine ligand compounds a...

Claims

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Application Information

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IPC IPC(8): C07F9/54
Inventor 谢应波张庆张华徐肖冰张维燕罗桂云
Owner 上海泰坦科技股份有限公司
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