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Method for synthesizing triphenylphosphine onium salts and halomethyl benzyl ethers compounds

The technology of a halomethyl benzyl ether and a synthesis method, which is applied in the field of organic compound synthesis, can solve the problems of low yield of triphenylphosphonium salts, low purity of intermediates, decomposition of unstable halogenated hydrocarbons, etc. High efficiency and purity, simple process and convenient operation

Inactive Publication Date: 2009-03-11
SHANGHAI CHEMPARTNER CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The technical problem to be solved by the present invention is to overcome the low purity of the triphenylphosphonium salt compound intermediates prepared by the existing method at 20-25°C, and the purification process will cause the decomposition of unstable halogenated hydrocarbons, Ultimately lead to the lower defect of the productive rate of triphenylphosphonium salts, and provide a kind of yield and purity higher, process is simple, the method for the triphenylphosphonium salts compound intermediate of easy operation, and in this Method for preparing triphenylphosphonium salt compounds based on the method

Method used

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  • Method for synthesizing triphenylphosphine onium salts and halomethyl benzyl ethers compounds
  • Method for synthesizing triphenylphosphine onium salts and halomethyl benzyl ethers compounds
  • Method for synthesizing triphenylphosphine onium salts and halomethyl benzyl ethers compounds

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Embodiment 1

[0019] In a 250 ml three-necked flask, a thermometer and a stirrer were installed, and hydrogen chloride gas (0.12 mol) was passed into benzyl alcohol (0.1 mol) and paraformaldehyde (0.1 mol), and the reaction temperature was controlled to -10°C. It was then stirred at this temperature for 5 hours. Then n-hexane (100ml) was added at room temperature to separate the layers, and the solvent was evaporated under reduced pressure to obtain the product as a light yellow liquid with a yield of 96% and a purity of 99.1area% (HPLC).

Embodiment 2

[0021] In a 250 ml three-necked flask, install a thermometer and a stirrer, feed 4-fluorobenzyl alcohol (0.1mol) and paraformaldehyde (0.15mol) into hydrogen bromide gas (0.15mol), and control the reaction temperature to -5°C . It was then stirred at this temperature for 4 hours. Then n-hexane (120ml) was added at room temperature to separate the layers, and the solvent was evaporated under reduced pressure to obtain the product as a light yellow liquid with a yield of 98% and a purity of 99.6area% (HPLC).

Embodiment 3

[0023] In a 250 ml three-necked flask, a thermometer and a stirrer were installed, and 4-chlorobenzyl alcohol (0.1mol) and paraformaldehyde (0.25mol) were fed into hydrogen chloride gas (0.14mol), and the reaction temperature was controlled at 0°C. It was then stirred at this temperature for 4 hours. Then n-hexane (110ml) was added at room temperature to separate the layers, and the solvent was evaporated under reduced pressure to obtain the product as a light yellow liquid with a yield of 92% and a purity of 99.2area% (HPLC).

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Abstract

The invention discloses a method for synthesizing triphenyl-phosphonium bromide salt and an intermediate halomethyl benzyl ether compound thereof. The method comprises the following steps that at a temperature of between 10 DEG C below zero and 10 DEG C, hydrogen chloride or hydrogen bromide and benzyl alcohol compound react with paraform to synthesize the halomethyl benzyl ether compound, and then the halomethyl benzyl ether compound reacts with triphenyl-phosphonium bromide in a solvent to obtain the triphenyl-phosphonium bromide salt compound. The method solves the problems that the purity of the halomethyl benzyl ether compound prepared at a temperature of between 20 DEG C and 25 DEG C by the prior method is low, and in the purification process, the intermediate is decomposed, which results in the low yield of the triphenyl-phosphonium bromide salt at the end. The triphenyl-phosphonium bromide salt and the intermediate halomethyl benzyl ether compound which are prepared by the method have the advantages of higher yield and purity without purification, simple process, convenient operation and higher industrial application value, and are easy to be applied to industrial scale production.

Description

technical field [0001] The invention belongs to the field of organic compound synthesis, and in particular relates to a synthesis method of a triphenylphosphonium salt compound and its intermediate halomethyl benzyl ether compound. Background technique [0002] In recent years, phenylphosphonium salt compounds have been widely used in drug synthesis as precursors of raw materials for olefin synthesis (ie Wittig reagent). The synthesis method of its intermediates is becoming more and more important. [0003] So far, the synthetic method of phenylphosphonium salt compound is mainly the method reported by D.S.Connor (Benzylchloromethyl ether, Org.Synth.Coll.Vol 6, 1998, p101; 1972, Vol 52, p16) et al. The reaction of alcohol, paraformaldehyde and hydrogen chloride produces halomethyl benzyl ether (triphenylphosphonium compound intermediate), which is then reacted with triphenylphosphine. Wherein the temperature of the first step reaction is normal temperature (20~25 ℃). But ...

Claims

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Application Information

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IPC IPC(8): C07C41/01C07F9/535
Inventor 刘国斌李原强胡祯全
Owner SHANGHAI CHEMPARTNER CO LTD
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