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Method for synthesizing bromodifluoromethyl selenide compound under metal-free condition

A technology of bromodifluoromethylselenide and difluoromethylselenide, which is applied in the field of chemical synthesis, can solve the problems of unfavorable large-scale popularization and application, narrow substrate range, complicated operation, etc., and achieve large-scale production and application, The effect of wide substrate universality and reduced operation difficulty

Active Publication Date: 2021-10-15
JIANGSU INST OF NUCLEAR MEDICINE
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The above methods all require the use of toxic selenium sources (benzeneselenol and potassium selenocyanate), complicated operations (requiring Schlenk technology and low temperature conditions), and relatively narrow substrate scope (systematic synthesis lacking alkyl-substituted substrates), which is very unfavorable Large-scale promotion and application

Method used

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  • Method for synthesizing bromodifluoromethyl selenide compound under metal-free condition
  • Method for synthesizing bromodifluoromethyl selenide compound under metal-free condition
  • Method for synthesizing bromodifluoromethyl selenide compound under metal-free condition

Examples

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Embodiment 1

[0058] Embodiment 1: the preparation of (bromodifluoromethyl) (2-phenoxyethyl) selenide

[0059] This embodiment provides the preparation method of (bromodifluoromethyl) (2-phenoxyethyl) selenide, and the specific synthesis steps are:

[0060] Take a clean 8mL screw-top reaction bottle, add a 5*10mm magnetic stirrer, take Se-(2-phenoxyethyl)selenobenzenesulfonate (1a, 136.5mg, 0.4mmol) and tetrabutyl bromide Ammonium (64.5 mg, 0.2 mmol) was dissolved in 2 mL of acetonitrile. Then (bromodifluoromethyl)trimethylsilane (2, 98 μL, 0.60 mmol) was added, the bottle was capped, stirred in an oil bath at 30° C. (500 rpm), and reacted for 30 minutes. After the reaction was over, the reaction system was transferred to an eggplant-shaped flask, and 800 mg of column chromatography silica gel powder was added, and the solvent was removed by rotary evaporation, and then the column chromatography was separated with sherwood oil as an eluting agent to obtain the target product (bromodifluoro...

Embodiment 2

[0066] Embodiment 2: the amplified synthesis of (bromodifluoromethyl) (2-phenoxyethyl) selenide

[0067] This embodiment provides a large-scale synthetic method of (bromodifluoromethyl) (2-phenoxyethyl) selenoether, and the specific synthetic steps are:

[0068] Take a clean 50mL round-bottomed reaction bottle, add a 20*10mm magnetic stirrer, take Se-(2-phenoxyethyl)selenobenzenesulfonate (1a, 1.365g, 4.0mmol) and tetrabutyl bromide Ammonium (0.645 g, 2.0 mmol) was dissolved in 20 mL of acetonitrile. Then (bromodifluoromethyl)trimethylsilane (2, 0.98 mL, 6.0 mmol) was added, and the bottle was capped, stirred in an oil bath at 30° C. (500 rpm), and reacted for 60 minutes. After the reaction finished, the reaction system was transferred to an eggplant-shaped flask, 2.0g column chromatography silica gel powder was added, the solvent was removed by rotary evaporation, and then the column chromatography separation was carried out with sherwood oil as a eluting agent to obtain the...

Embodiment 3

[0070] Embodiment 3: Preparation of (bromodifluoromethyl) (2-(4-methoxyphenoxy) ethyl) selenoether

[0071] This embodiment provides the preparation method of (bromodifluoromethyl)(2-(4-methoxyphenoxy)ethyl)selenoether, the specific synthesis steps are:

[0072] Take a clean 8mL screw-top reaction bottle, add a 5*10mm magnetic stir bar, and take Se-(2-(4-methoxyphenoxy)ethyl)selenobenzenesulfonate (1b, 148.5mg, 0.4mmol ) and tetrabutylammonium bromide (64.5 mg, 0.2 mmol) were dissolved in 2 mL of acetonitrile. Then (bromodifluoromethyl)trimethylsilane (2, 98 μL, 0.60 mmol) was added, the bottle was capped, stirred in an oil bath at 30° C. (500 rpm), and reacted for 30 minutes. After the reaction was over, the reaction system was transferred to an eggplant-shaped flask, and 800 mg of silica gel powder for column chromatography was added. / v) As eluent, perform column chromatography separation to obtain the target product (bromodifluoromethyl)(2-(4-methoxyphenoxy)ethyl)selenid...

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Abstract

The invention relates to a method for synthesizing a bromodifluoromethyl selenide compound under a metal-free condition, and belongs to the technical field of chemical synthesis. The invention provides the method for synthesizing the bromodifluoromethyl selenide compound, wherein the method is characterized in that the synthesis of the bromodifluoromethyl selenide compound is realized under a metal-free condition by taking a seleno-benzenesulfonate substrate as an electrophilic selenium reagent and utilizing a difluorocarbene reaction strategy. The selenobenzene sulfonate substrate used in the method is low in toxicity, easy to prepare and preserve and excellent in reaction activity; and compared with the prior art, the method does not need to use selenium-containing compounds (such as benzeneselenol, potassium selenide and other toxic selenium sources) which are unstable in property and high in toxicity, and the safety of the chemically synthesized bromodifluoromethyl selenide compound is obviously improved.

Description

technical field [0001] The invention relates to a method for synthesizing bromodifluoromethyl selenide compounds under metal-free conditions, belonging to the technical field of chemical synthesis. Background technique [0002] Organic fluorine-containing compounds can regulate the chemical reactivity, solubility, lipophilicity and metabolic stability of organic molecules by introducing fluorine atoms into the molecular structure. At present, gem-difluoromethylene compounds in organic fluorine-containing compounds have shown important application value in medicinal chemistry research (gem-difluoromethyl compounds with biopharmaceutical activity can be seen in detail figure 1 ), and among organic fluorine-containing compounds, bromodifluoromethyl selenide compound (R-SeCF 2 Br) has received the most attention. [0003] As good halogen bond donors, bromodifluoromethyl selenide compounds have broad application prospects in the field of crystal engineering. Moreover, the C-Br...

Claims

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Application Information

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IPC IPC(8): C07C391/00C07C391/02C07D211/96C07D277/72C07D333/40
CPCC07C391/00C07C391/02C07D211/96C07D277/72C07D333/40
Inventor 方毅李欣刘春仪唐婕陈正平
Owner JIANGSU INST OF NUCLEAR MEDICINE
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