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Preparation process of (bromomethyl) trifluoro potassium borate

A technology of potassium trifluoroborate and preparation process, which is applied in the fields of compounds containing elements of Group 3/13 of the periodic table, chemical instruments and methods, organic chemistry, etc. problem, to achieve the effect of low cost, simple operation and improved yield

Inactive Publication Date: 2015-03-25
CHEN STONE GUANGZHOU CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] The disadvantage of the prior art is that it needs to be carried out at ultra-low temperature, and the production cost is too high, and if the temperature is higher than 50 degrees in the reaction, the reaction intermediate bromomethyl borate lithium salt will be decomposed, resulting in multiple Impurities reduce the yield and make purification difficult
Therefore, this process is not suitable for industrial scale-up production, resulting in limited application

Method used

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  • Preparation process of (bromomethyl) trifluoro potassium borate

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preparation example Construction

[0024] A preparation technique for (bromomethyl) potassium trifluoroborate, comprising the following steps:

[0025] 1) Add n-butyllithium, azaborane and organic solvent into the reaction vessel;

[0026] 2) Add dibromomethane dropwise within 1.5-3.5 hours to react, and control the temperature of the system at -20°C-30°C;

[0027] 3) Add KHF at 20-30°C 2 The aqueous solution is reacted at 80-100°C for 6-10h;

[0028] 4) Separation and purification of the reaction system in the previous step to obtain the product.

[0029] The structural formula of described nitrogen borane is as follows:

[0030] ; ; ; ;

[0031] Among them, R 1 , R 2 , R 3 , R 4 For independent protecting group, X is chlorine or bromine, n=1~5.

[0032] The protecting group (i.e. R 1 , R 2 , R 3 , R 4 ) is selected from the following groups: methyl, ethyl, n-propyl, isopropyl, allyl, n-butyl, isobutyl, tert-butyl, 2-enyl, 3-enyl, 2 -Methyl-2-allyl, n-pentyl, 1-methylbutyl, 2-methylbutyl,...

Embodiment 1

[0040] In a dry 500 mL four-necked reaction flask, add 80 mL of 2.5M / L n-butyllithium, 27 g of bis(dimethylamino)chloroborane ( ) and 200 mL THF were added to the reaction flask. Then start to drop 1.0 g of dibromomethane at room temperature, and stir for half an hour. Continue to drop 28 g of dibromomethane for 2 hours, and control the temperature of the reaction solution at 15°C. Then add 33 g KHF at room temperature 2100 mL of the aqueous solution, the temperature is controlled at 80-100 degrees and the stirring is continued for 8 hours. After the reaction was monitored by TLC, the reaction solution was concentrated under reduced pressure. The residue was dissolved and filtered with 120 mL of acetone, and the mother liquor was concentrated under reduced pressure. The resulting residue was slurried with 100 mL of methyl tert-butyl ether and filtered. The wet product was vacuum-dried to obtain 15.6 g (bromomethyl) potassium trifluoroborate with a yield of 70%. The char...

Embodiment 2

[0042] In a dry 500 mL four-necked reaction flask, 80 mL of 2.5M / L n-butyllithium, 27 g of bis(dimethylamino)chloroborane ( ) and 200 mL of ether were added to the reaction flask. Then start to drop 1.0 g of dibromomethane at room temperature, and stir for half an hour. Continue to drop 28 g of dibromomethane for 2 hours, and control the temperature of the reaction solution at 10°C. Then add 33 g KHF at room temperature 2 100 mL of aqueous solution and 100 mL of tetrahydrofuran, and the temperature was controlled at 80-100 degrees to continue stirring for 8 hours. After the reaction was monitored by TLC, the reaction solution was concentrated under reduced pressure. The residue was dissolved and filtered with 120 mL of acetone, and the mother liquor was concentrated under reduced pressure. The resulting residue was slurried with 100 mL of methyl tert-butyl ether and filtered. The wet product was vacuum-dried to obtain 14.8 g (bromomethyl) potassium trifluoroborate with a...

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Abstract

The invention discloses a preparation process of (bromomethyl) trifluoro potassium borate. The preparation process is characterized by comprising the following steps: 1) adding n-butyllithium, nitrogen borane and an organic solvent into a reaction container; 2) dropwise adding the residual dibromomethane within 1.5-2.5 hours to react, and controlling the temperature of a control system at (-20)-30 DEG C; 3) further adding an aqueous solution of KHF2 at 20-30 DEG C and carrying out reaction for 6-10 hours at 80-100 DEG C; and 4) carrying out separation and purification on the reaction system in the above step to obtain a product. According to the preparation process disclosed by the invention, dibromomethane is dropwise added into nitrogen borane and n-butyllithium, so that the Grignard reagent is generated while being consumed, thereby avoiding the safety risk brought by accumulation of the Grignard reagent and further avoiding the self coupled reaction thereof, and improving the yield. Therefore, the raw materials are easily available, the method is simple to operate, mild in reaction condition, green and environment-friendly in process, low in cost and high in yield. The process disclosed by the invention is suitable for industrial amplified production.

Description

technical field [0001] The invention relates to a preparation process of potassium (bromomethyl)trifluoroborate. Background technique [0002] The application of organic boronic acid and its derivatives has been a hot spot in the research and development of drugs and intermediates by major pharmaceutical companies for many years. Its use can greatly reduce the number of synthesis steps, speed up the development of new drugs, and greatly reduce energy consumption and cost. , Reduce the discharge of waste liquid, waste gas and waste residue developed by the traditional pharmaceutical industry. The 2010 Nobel Prize in Chemistry was awarded to Suzuki, the chemist who first developed and applied organoboronic acid. More than half of the currently developed new drugs are synthesized using organoboron reagents. Therefore, no matter whether organoboron reagents are directly used as innovative drugs or as pharmaceutical intermediates, they have a wide range of applications and huge ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02
CPCC07F5/025
Inventor 郎丰睿
Owner CHEN STONE GUANGZHOU CO LTD
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