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Synthesis method of triphenylphosphine derivative tri-(R-phenyl) phosphine

A synthetic method and phenyl technology, applied in the field of organic synthesis, can solve problems such as unsatisfactory yield, reaction quenching and the like

Pending Publication Date: 2020-10-27
江苏富比亚化学品有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0013] The above methods all have the problem that the yield is not satisfactory enough or that additional iodine is needed to initiate the reaction, or that additional reactants need to be added after the Grignard reaction is carried out, which easily leads to the problem of quenching of the reaction. Therefore, there is an urgent need for a yield Preparation method of tri-substituted phenylphosphine capable of continuous and stable reaction without adding additional initiator

Method used

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  • Synthesis method of triphenylphosphine derivative tri-(R-phenyl) phosphine
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  • Synthesis method of triphenylphosphine derivative tri-(R-phenyl) phosphine

Examples

Experimental program
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Effect test

Embodiment 1

[0050] Continuously feed dry nitrogen into the clean reactor, and add 4.86 g (0.2 mol) of magnesium chips, 3.80 g (0.03 mol) of p-chlorotoluene, and 15.33 g of solvent into the reactor. The temperature was raised with stirring, and the reaction was initiated at 42°C.

[0051] The pre-prepared p-chlorotoluene solution (21.52g (0.17mol) p-chlorotoluene, 65.02g 2-methyltetrahydrofuran) was added dropwise, and the temperature was controlled at about 55°C. After adding for 1 hour, cool down to about 25°C after adding and keeping warm for 1 hour.

[0052] Maintain the temperature of the kettle at about 25°C, add the pre-prepared phosphorus trichloride solution (phosphorus trichloride 8.25g (0.18mol), 2-methyltetrahydrofuran 20.21g) dropwise, add it for 1 hour, keep it warm for 1 hour and then cool it down for use .

[0053] Maintain the pressure of about -0.3MPa in the kettle, slowly increase the temperature of the kettle, and the inner temperature reaches about 85°C in about 1 ho...

Embodiment 2

[0057] Dry nitrogen was continuously fed into the clean reactor, and 19.44 g (0.8 mol) of magnesium chips, 11.97 g (0.064 mol) of p-bromoanisole, and 60.33 g of tetrahydrofuran were added to the reactor. The temperature was raised with stirring, and the reaction was initiated at 42°C.

[0058] Add the pre-prepared p-bromoanisole solution (137.66 g (0.736 mol) p-bromoanisole, 260.03 g tetrahydrofuran) dropwise, and control the temperature to about 55°C. After adding for 1 hour, keep warm for 1 hour and cool down for later use.

[0059] Maintain the temperature of the kettle at about 25°C, add the pre-prepared phosphorus trichloride solution (phosphorus trichloride 33.05g, tetrahydrofuran 80.21g) dropwise, add it in 1 hour, keep it warm for 1 hour, and cool it down for use.

[0060] Maintain the pressure of about -0.4MPa in the kettle, slowly increase the temperature of the kettle for about 1.5 hours, and the inner temperature reaches about 85°C. After the precipitation is comp...

Embodiment 3

[0064] The specific operation is the same as in Example 1, except that 0.06 mol of p-chlorotoluene is added in step 1. When the temperature is raised to 42° C., the reaction is very violent, resulting in flushing.

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Abstract

The invention relates to a synthesis method of a triphenylphosphine derivative tri-(R-phenyl) phosphine. The synthesis method comprises the following steps: adding magnesium chips, a solvent and R-substituted halobenzene into a reaction kettle under the protection of nitrogen, initiating a reaction at a proper temperature, and dropwise adding an R-substituted halobenzene solution to synthesize anintermediate; dropwise adding a phosphorus trichloride solution to complete a Grignard reaction; dropwise adding diluted hydrochloric acid for hydrolysis after negative-pressure desolvation; and carrying out post-treatment to obtain TRPP. According to the method, the tri-(R-phenyl) phosphine of which the purity is greater than 99% is obtained with high selectivity and high yield.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a synthesis method of triphenylphosphine derivative tri-(R-phenyl)phosphine. Background technique [0002] Triphenylphosphine and triphenylphosphine derivatives are organophosphorus compounds that have been studied more in recent years. Tri-(R-phenyl)phosphine (TRPP) is an important derivative of triphenylphosphine and can be used as the basic raw material of rhodium-phosphine complex catalyst, and also has a wide range of applications in domestic petrochemical industry. It is also widely used in pharmaceutical industry, organic synthesis, analysis and other fields. [0003] At present, the synthesis methods of tri-(R-phenyl)phosphine mainly include Grignard method, sodium method, Friedel-Crafts method, reduction method and the like. [0004] The Grignard method is to use halogenated benzene and metal magnesium in tetrahydrofuran solvent to make phenylmagnesium halide, and then...

Claims

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Application Information

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IPC IPC(8): C07F9/50
CPCC07F9/5022C07F9/5068
Inventor 薛磊李焕成吴邦元张召举
Owner 江苏富比亚化学品有限公司
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