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Alkyl trifluoromethyl thioether compound and preparation method thereof

A technology of alkyl trifluoromethyl sulfide and trifluoromethyl sulfide, which is applied in the field of alkyl trifluoromethyl sulfide compounds and their preparation, and can solve the problems of high cost, harsh reaction conditions, high difficulty and the like

Active Publication Date: 2015-04-29
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0014] The technical problem to be solved by the present invention is to overcome the existing problems in the existing method for synthesizing alkyl trifluoromethyl sulfides, the substrate needs to be pre-functionalized, the reaction conditions are harsh, the trifluoromethyl thio reagent is not easy to obtain, and the cost High, difficult and unsuitable for technical problems such as industrial production, and provide an alkyl trifluoromethyl sulfide compound and its preparation method

Method used

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  • Alkyl trifluoromethyl thioether compound and preparation method thereof
  • Alkyl trifluoromethyl thioether compound and preparation method thereof
  • Alkyl trifluoromethyl thioether compound and preparation method thereof

Examples

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Effect test

example 1

[0048] Example 1 C-H direct trifluoromethylthiolation reaction of cyclooctane, silver trifluoromethylthio and potassium persulfate

[0049]

[0050] Add silver trifluoromethylthio (0.5mmol), N-hydroxyphthalic acid imide (0.1mmol) and potassium persulfate (1.0mmol) into the reaction flask, add cyclooctane (1.0mmol) after pumping argon three times mmol) and acetonitrile (5 mL). The reaction bottle was placed in an oil bath at 80°C and started to heat and stir for 4 hours, then took it out, and cooled to room temperature. With benzotrifluoride as the internal standard substance, using 19 F-NMR confirmed the formation of cyclooctyl trifluoromethyl sulfide (yield 82%). The reaction solution was filtered, and the filtrate was used to remove the solvent by a rotary evaporator, and separated by bottle-neck-bottle distillation to obtain a colorless oily liquid (64 mg, yield 60%). The relevant data are as follows: 1 H NMR (400MHz, CDCl 3 ): δ3.51-3.44(m,1H),2.09-2.02(m,2H),1.80-...

Embodiment 2

[0051] Example 2 The decarboxylation trifluoromethylthiolation of cyclohexanecarboxylic acid, silver trifluoromethylthio and potassium persulfate

[0052]

[0053]Silver trifluoromethylthio (1.5mmol), pyridine (0.1mmol) and potassium persulfate (4.5mmol) were added to the reaction flask, and cyclohexanecarboxylic acid (1.0mmol) and acetonitrile (20mL) were added after argon was pumped three times. Place the sealed tube in an oil bath at 60°C and start heating and stirring for 24 hours, then take it out, and let it cool to room temperature. With benzotrifluoride as the internal standard substance, using 19 F-NMR confirmed the formation of cyclohexyltrifluoromethylsulfide (83% yield). Formation of this product was also confirmed by GC-MS. The relevant data are as follows: m / z=184 (GC-MS; EI).HRMS-EI: Calculated for C 7 h 11 f 3 S:184.0534,Found:184.0535.Crude 1 H NMR (400MHz, CD 3 CN): δ3.35(tt,J=4Hz,1H),2.06-1.27(m,10H)ppm.Crude 19 F NMR (376MHz, CD 3 CN):δ-39.78(s,...

Embodiment 3

[0054] Coupling reaction of embodiment 3 cyclodecyl boronic acid, silver trifluoromethylthio and potassium persulfate

[0055]

[0056] Add silver trifluoromethylthio (0.5mmol), o-phenanthroline (0.5mmol) and potassium persulfate (1.0mmol) into the reaction flask, add cyclodecylboronic acid (3.0mmol) and Acetonitrile (15 mL). Place the sealed tube in an oil bath at 25°C and start heating and stirring for 36 hours, then take it out, and wait to cool to room temperature. With benzotrifluoride as the internal standard substance, using 19 It was confirmed by F-NMR that cyclodecyltrifluoromethylsulfide was produced (yield: 74%). The reaction solution was filtered, and the filtrate was used to remove the solvent by a rotary evaporator, and separated by bottle-neck-bottle distillation to obtain a colorless oily liquid (65 mg, yield 55%). The relevant data are as follows: 1 H NMR (400MHz, CDCl 3 ):δ3.58-3.51(m, characteristic CH-SCF 3 ),1.97-1.79(m,4H),1.65-1.63(m,4H).1.54-1....

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Abstract

The invention discloses an alkyl trifluoromethyl thioether compound and a preparation method thereof. The alkyl trifluoromethyl thioether compound comprises the following step: under protection of inertial gas, carrying out trifluoromethylthiolation reaction on an alkyl primer and a trifluoromethylthio reagent to obtain the alkyl trifluoromethyl thioether compound. The trifluoromethylthio reagent comprises the following components: a metal salt containing trifluoromethylthio, an oxidizing agent and a nitrile solvent. The trifluoromethylthio reagent disclosed by the invention is low in price and easily available. When the trifluoromethylthio reagent is used for synthesizing the alkyl trifluoromethyl thioether compound, the trifluoromethylthio can be quickly and conveniently introduced to the alkyl primer which is not pre-functionalized. Moreover, the synthetic method is wide in range of application of the primer, mild in reaction condition, high in reaction efficiency, mostly direct in reaction, simple to operate, low in cost and more suitable for industrial production.

Description

technical field [0001] The invention relates to an alkyl trifluoromethyl sulfide compound and a preparation method thereof. Background technique [0002] Fluorine atom is the ninth element in the periodic table and belongs to group VIIA. Its atomic radius is close to that of hydrogen atom and has the strongest electronegativity. The C-F bond has a high bond energy, and the bond length is the closest to the C-H bond length. . It is precisely because of these characteristics of fluorine atoms that fluorine-containing organic compounds exhibit a series of unique physical and chemical properties, which have very important application values ​​in the fields of medicine, pesticides, and materials. Currently, 20% to 30% of pharmaceuticals and 30% to 40% of agricultural chemicals contain at least one fluorine atom. Among various fluorine-containing functional groups, trifluoromethylthio (-SCF 3 ) plays an important role due to its strong electronegativity and strong lipophilicity...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B45/06C07C319/14C07C323/03C07C323/22C07C323/12C07C323/13C07D209/48
Inventor 陈庆云刘超吴浩肖智伟
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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