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Preparation method of tri(pentafluorophenyl) borane

A kind of technology of pentafluorophenyl and pentafluorobromobenzene, applied in the field of preparation of triborane, can solve problems such as high price, application has not been paid enough attention, etc., and achieve the effect of reducing production cost

Inactive Publication Date: 2013-09-18
SHANGHAI SINOFLUORO SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Tris(pentafluorophenyl)borane (B(C 6 f 5 ) 3 , TPFPB) was prepared by Massey and Park as early as 1964, but after more than 20 years B (C 6 f 5 ) 3 application has not received enough attention
However, there is no domestic manufacturer of pentafluorobenzene used in this route, and foreign manufacturers are expensive

Method used

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  • Preparation method of tri(pentafluorophenyl) borane
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  • Preparation method of tri(pentafluorophenyl) borane

Examples

Experimental program
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Embodiment 1

[0025] After adding pentafluorobromobenzene (0.09mol, 22.2g) into a three-necked flask (250mL), 2-methyltetrahydrofuran (100mL) was added. At 25°C, n-BuLi (2.5M, 0.09mol, 36mL) was added dropwise. After reacting for 6.0h, trimethyl borate (0.03mol, 3.1g) was added dropwise at 25°C for 10min. After 16 h at 25°C, the reaction was monitored by GC. Pour the reaction solution into water, extract twice with 2-methyltetrahydrofuran, combine the organic layers, wash twice with water and once with saturated brine, dry the organic layer with sodium sulfate, evaporate 2-methyltetrahydrofuran under reduced pressure, and recover 2-Methyltetrahydrofuran was obtained as a crude product, which was recrystallized from n-hexane to obtain tris(pentafluorophenyl)borane (0.0049mol, 2.48g), with a yield of 16.2%.

Embodiment 2

[0027] After adding pentafluorobromobenzene (0.09mol, 22.2g) into a three-necked flask (250mL), 2-methyltetrahydrofuran (100mL) was added. EtMgBr (1.0M, 0.09mol, 90mL) was added dropwise at 25°C. After reacting for 6.0h, trimethyl borate (0.03mol, 3.1g) was added dropwise at 25°C for 10min. After 16 h at 25°C, the reaction was monitored by GC. Pour the reaction solution into water, extract twice with 2-methyltetrahydrofuran, combine the organic layers, wash twice with water and once with saturated brine, dry the organic layer with sodium sulfate, evaporate 2-methyltetrahydrofuran under reduced pressure, and recover 2-Methyltetrahydrofuran was obtained as a crude product, which was recrystallized from n-hexane to obtain tris(pentafluorophenyl)borane (0.0125 mol, 6.40 g), with a yield of 41.7%.

Embodiment 3

[0029] After adding pentafluorobromobenzene (0.09mol, 22.2g) into a three-necked flask (250mL), diethyl ether (100mL) was added. At 25°C, i-PrMgCl (2.0M, 0.09mol, 45mL) was added dropwise. After reacting for 6.0h, trimethyl borate (0.03mol, 3.1g) was added dropwise at 25°C for 10min. After 16 h at 25°C, the reaction was monitored by GC. Pour the reaction solution into water, extract twice with 2-methyltetrahydrofuran, combine the organic layers, wash twice with water and once with saturated brine, dry the organic layer with sodium sulfate, evaporate 2-methyltetrahydrofuran under reduced pressure, and recover 2-Methyltetrahydrofuran was obtained as a crude product, which was recrystallized from n-hexane to obtain tris(pentafluorophenyl)borane (0.0182mol, 9.28g), with a yield of 60.5%.

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Abstract

The invention provides a preparation method of tri(pentafluorophenyl) borane. The method comprises the following steps: by using pentafluorobromobenzene as a raw material, dissolving the raw material in an organic solvent; adding strong base at a certain temperature; reacting to obtain an intermediate; and performing a reaction on the intermediate and trimethyl borate for a period of time to obtain tri(pentafluorophenyl) borane. The preparation method provided by the invention has the characteristics of shorter reaction process, simpleness and convenience in operation and lower cost of raw materials.

Description

technical field [0001] The invention relates to the technical field of organic chemical synthesis, in particular to a preparation method of tris(pentafluorophenyl)borane. Background technique [0002] Tris(pentafluorophenyl)borane (Tris(pentafluorophenyl)borane) has the advantages of stable chemical properties, strong acidity, and convenient use compared with traditional Lewis acids, and is called a non-traditional Lewis acid. The application field of tris(pentafluorophenyl)borane has been developed from the initial olefin polymerization co-catalyst to other fields of organic chemistry and polymer chemistry. The reaction catalyzed by tris(pentafluorophenyl)borane is quite different from the reaction catalyzed by traditional Lewis acid in the reaction mechanism and reaction result. [0003] Tris(pentafluorophenyl)borane is a strong Lewis acid, which is more acidic than BF 3 Stronger than BCl 3 weak. Tris(pentafluorophenyl)borane is a powdery solid, which can exist stably ...

Claims

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Application Information

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IPC IPC(8): C07F5/02
Inventor 王小进王伟力张巍
Owner SHANGHAI SINOFLUORO SCI
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