Preparation method of tris(2-furyl) phosphine

A technology of furyl and furan, which is applied in the field of preparation of triphosphorus, can solve the problems of low yield and high cost of raw materials, and achieve the effects of reducing production cost, enhancing lithiation ability, and complete lithiation reaction

Active Publication Date: 2013-04-03
PANJIN GELIN KAIMO TECH CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The reactions of each step of the synthetic route are relatively stable and easy to

Method used

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  • Preparation method of tris(2-furyl) phosphine
  • Preparation method of tris(2-furyl) phosphine
  • Preparation method of tris(2-furyl) phosphine

Examples

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preparation example Construction

[0033] (1) Preparation of lithium furyl

[0034] Replace the reaction bottle with an inert gas such as a nitrogen atmosphere, and add furan, tetramethylethylenediamine and n-hexane to the reaction bottle under mechanical stirring. The amount of solvent n-hexane is usually added according to the ratio of 500 mL of n-hexane required for 1 mol of furan; At room temperature, add dropwise the butyllithium with a concentration of 1.3-2.5M / L, wherein the mol ratio of butyllithium to furan can be 1:0.9-1, and the mol ratio of butyllithium to tetramethylethylenediamine can be 1:1-2, after the dropwise addition, raise the temperature to 40-60°C, preferably to 45-55°C, keep it for 0.5-3 hours, preferably keep it warm for 1-2 hours.

[0035] (2) Preparation of tri(2-furyl)phosphorus

[0036] Add the n-hexane solution of phosphorus trihalide dropwise to the generated lithium furyl at -10-0°C. The amount of n-hexane as a solvent is usually added in the proportion that 1 mol of phosphorus t...

Embodiment 1

[0048] The reaction flask was replaced with a nitrogen atmosphere, and under mechanical stirring, 20 g of analytically pure furan, 34.8 g of analytically pure TMEDA and 140 mL of n-hexane were added to the reaction flask, and at room temperature, a concentration of 2.5 M / L n-butyl lithium ( Analytical pure) 120mL, after the dropwise addition, the temperature was raised to 50°C and kept for 2h.

[0049] Add analytically pure PCl dropwise at 0°C 3 8g of n-hexane 50mL solution, after the dropwise addition is completed, keep at this temperature for 1h, naturally rise to room temperature, and stir for 5h.

[0050] Pour the reaction solution into 200mL of saturated ammonium nitrate aqueous solution, after fully stirring, let it stand for stratification, separate the organic phase, extract the aqueous phase with dichloromethane for 2-3 times, combine the organic phase, and concentrate the organic phase to obtain the crude product. The product was recrystallized with petroleum ether ...

Embodiment 2

[0055] Replace the reaction bottle into a nitrogen atmosphere, add 20g of analytically pure furan, 27.9g of analytically pure TMEDA and 140mL of n-hexane to the reaction bottle under mechanical stirring, and add 120mL of n-butyllithium with a concentration of 2.5M / L dropwise at room temperature , after the dropwise addition was completed, the temperature was raised to 50°C for 2h.

[0056] Add analytically pure PCl dropwise at 0°C 3 8g of n-hexane 50mL solution, after the dropwise addition is completed, keep at this temperature for 1h, naturally rise to room temperature, and stir for 5h.

[0057] Pour the reaction solution into 200mL of saturated ammonium nitrate aqueous solution, after fully stirring, let it stand for stratification, separate the organic phase, extract the aqueous phase with dichloromethane for 2-3 times, combine the organic phase, and concentrate the organic phase to obtain the crude product. The product was recrystallized with petroleum ether to obtain 10....

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Abstract

The invention relates to a preparation method of tris(2-furyl) phosphine, which comprises the following steps of: in the atmosphere of inert gas, at the room temperature, dripping a butyl lithium solution in a normal hexane solution containing furan and tetramethylethylenediamine, raising the temperature to 40-60 DEG C, and keeping for 0.5-3 hours to produce a furyl lithium reagent; dripping phosphorus halide in the normal hexane solution at the temperature of minus 10 to 0 DEG C, carrying out heat insulation for 0.5-2 hours, naturally raising the temperature to the room temperature, and stirring for 1-8 hours; and pouring a reaction solution into a saturated strong acidic-weak basic inorganic salt solution, concentrating an organic phase to obtain a crude product, and then recrystallizing with of petroleum ether to obtain tris(2-furyl) phosphine. With the adoption of the preparation method, the preparation cost is greatly lowered, the yield is greatly increased, and the product purity is high. In the embodiment of the invention, anhydrous cerium trichloride is added into produced furyl lithium to obtain an organic cerium reagent, and the organic cerium reagent is further reacted with phosphorus trihalide, so the yield can be further increased, and the by-products can be reduced.

Description

technical field [0001] The invention relates to a preparation method of tris(2-furyl)phosphorus, which belongs to the technical field of organic synthesis. Background technique [0002] Tris(2-furyl)phosphorus is mainly used as a phosphine ligand in transition metal-mediated organic synthesis, and is also used in Wittig reactions, playing a wide range of roles in modern organic synthesis and practical applications. [0003] At present, the main method of synthesizing tris(2-furyl)phosphorus is to prepare Grignard reagent with 2-bromofuran as raw material, then dropwise add the tetrahydrofuran solution of phosphorus trichloride at 0°C, stir for 2 hours after the dropwise addition, and react After completion, pour into saturated aqueous ammonium chloride solution, let stand to separate layers, concentrate the organic phase, and recrystallize the obtained crude product with petroleum ether to obtain a white crystal product. The reactions of each step of the synthetic route are...

Claims

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Application Information

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IPC IPC(8): C07F9/655
Inventor 宫宁瑞
Owner PANJIN GELIN KAIMO TECH CO LTD
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