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Method for synthesizing di-tert-butylphenylphosphonium tetrafluoroborate

A technology of di-tert-butylphenyl and tetrafluoroboric acid, which is applied in the synthesis of organic phosphine compounds and the synthesis of di-tert-butylphenylphosphonium tetrafluoroborate, which can solve the difficulties of post-processing and affect the reaction yield, etc. problem, to achieve the effect of simple operation, simplified experimental steps and high yield

Active Publication Date: 2019-03-08
HENAN ACADEMY OF SCI CHEM RES INST CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The main disadvantage of the above method is that the cuprous catalyst used can complex with the product di-tert-butylphenylphosphine, which causes difficulties in post-processing and affects the yield of the reaction.

Method used

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  • Method for synthesizing di-tert-butylphenylphosphonium tetrafluoroborate

Examples

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Embodiment 1

[0013] Example 1: Synthesis of di-tert-butylphenylphosphonium tetrafluoroborate

[0014] Under the protection of argon, add 1L of toluene to the dry reactor, then add phenylphosphine dichloride (178 g, 1mol), and add 2L of 1.0 M diisobutylaluminum hydride toluene solution dropwise at 0~10 ºC , then heated up to 20-40 ºC for 8 hours, then added 2L of 1N sodium hydroxide solution to quench the reaction, then separated, extracted, and the organic layer was dried with anhydrous magnesium sulfate, and the organic phase was transferred to another dry reaction After the reactor, tert-butanol (148 g, 2 mol) and 47% by mass boron trifluoride ether solution (1.5 kg, 5 mol) were added successively, and after 10 hours of reaction at 20-40 ºC, water was added to quench the reaction. Precipitation was formed, filtered by suction, and the obtained solid was vacuum-dried to obtain 288 g of di-tert-butylphenylphosphonium tetrafluoroborate, with a yield of 93%; 31 P NMR (162 MHz, CDCl 3 , ppm...

Embodiment 2

[0015] Example 2: Synthesis of di-tert-butylphenylphosphonium tetrafluoroborate

[0016] Under the protection of argon, add 1L of toluene to the dry reactor, then add phenylphosphine dichloride (178 g, 1mol), and add 3L of 1.0 M diisobutylaluminum hydride toluene solution dropwise at 0~10 ºC , then heated up to 20-40 ºC for 6 hours, then added 2L of 1N sodium hydroxide solution to quench the reaction, then separated, extracted, the organic layer was dried with anhydrous magnesium sulfate, and the organic phase was transferred to another dry reaction After the reactor, tert-butanol (222 g, 3 mol) and boron trifluoride ether solution (3 kg, 10 mol) with a mass percentage of 47 % were added successively, and after reacting at 20-40 ºC for 10 hours, water was added to quench the reaction. Precipitation was formed, filtered with suction, and the obtained solid was vacuum-dried to obtain 282 g of di-tert-butylphenylphosphonium tetrafluoroborate, with a yield of 91%.

Embodiment 3

[0017] Example 3: Synthesis of di-tert-butylphenylphosphonium tetrafluoroborate

[0018] Under the protection of argon, add 1L of toluene to the dry reactor, then add phenylphosphine dichloride (178 g, 1mol), and add 3L of 1.0 M diisobutylaluminum hydride toluene solution dropwise at 0~10 ºC , then heated up to 20-40 ºC for 8 hours, then added 2L of 1N sodium hydroxide solution to quench the reaction, then separated, extracted, and the organic layer was dried with anhydrous magnesium sulfate, and the organic phase was transferred to another dry reaction After the reactor, tert-butanol (222 g, 3 mol) and 47% by mass boron trifluoride ether solution (1.8 kg, 6 mol) were added successively, and after 12 hours of reaction at 20-40°C, water was added to quench the reaction. Precipitation was formed, filtered with suction, and the obtained solid was vacuum-dried to obtain 288 g of di-tert-butylphenylphosphonium tetrafluoroborate, with a yield of 93%.

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Abstract

The invention discloses a method for synthesizing di-tert-butylphenylphosphonium tetrafluoroborate, and belongs to the field of organic synthesis. The method comprises the following steps: in the anhydrous and anaerobic atmospheres, taking dichlorophenylphosphine as a raw material, after the reduction of diisobutyl aluminium hydride, reacting with tertiary butanol under the catalytic action of boron trifluoride, and then carrying out hydrolysis to generate the di-tert-butylphenylphosphonium tetrafluoroborate. Compared with the prior art, the method is high in yield and simple in aftertreatment, and is more applicable for industrial production.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and relates to a synthesis method of a class of organic phosphine compounds, in particular to a synthesis method of di-tert-butylphenylphosphonium tetrafluoroborate. Background technique [0002] Coupling reaction is an effective method for forming C-C, C-N bonds in organic synthesis, and it has a very wide range of applications in the synthesis of natural products, functional materials, drugs, liquid crystal molecules and biologically active compounds. The two key factors that determine the catalytic effect of a catalyst are the electron density and the steric volume effect of the ligand. Organophosphine ligands are commonly used ligands to catalyze coupling reactions, and their electronic and spatial structures have obvious modulation effects on transition metal coordination catalysts. Di-tert-butylphenylphosphine has high reactivity in palladium-catalyzed Suzuki, Negishi, Stille, Heck and oth...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/50
CPCC07F9/5072
Inventor 孙敏青化林陈瑨吴威张垚陈辉屈凤波杨瑞娜
Owner HENAN ACADEMY OF SCI CHEM RES INST CO LTD
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