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Preparation method and application of aryl trifluoromethyl compound

A technology of aryl trifluoromethyl and trifluoromethyl, which is applied in the field of preparation of aryl trifluoromethyl compounds, can solve the problems of complex products in the process, catalyst residue, harsh preparation conditions, etc., and achieve the effect of simple reaction conditions

Inactive Publication Date: 2018-06-22
深圳蓝新科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the present invention is to overcome the above-mentioned deficiencies of the prior art, and to provide a preparation method of aryl trifluoromethyl compounds to solve the problem of harsh preparation conditions, complicated process and catalyst residues in the existing aryl trifluoromethyl compounds. and other technical issues

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  • Preparation method and application of aryl trifluoromethyl compound
  • Preparation method and application of aryl trifluoromethyl compound
  • Preparation method and application of aryl trifluoromethyl compound

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preparation example Construction

[0032] The embodiment of the present invention provides a preparation method of an aryl trifluoromethyl compound, which at least includes the following steps:

[0033] Under light conditions and alkaline conditions, compound A and a trifluoromethyl reagent are reacted in an organic solvent system containing a catalyst to obtain an aryl trifluoromethyl compound;

[0034] Wherein the structural formula of compound A is as follows:

[0035]

[0036] The R in the structural formula of the compound A is one or more of alkyl, halogen, nitro, alkoxy, hydroxyl, and carboxyl.

[0037] The preparation method of the aryl trifluoromethyl compound of the present invention will be further explained in detail below.

[0038] In the light conditions of the present invention, the preferred light wavelength is 430nm-550nm. Under the light irradiation of this wavelength, the catalysis of the transition metal copper or palladium complex is not required, and no specific functional group is use...

Embodiment 1

[0060] This embodiment provides a preparation method of 4-trifluoromethylphenol. The structural formula of this 4-trifluoromethylphenol is as shown in molecular structural formula I1:

[0061]

[0062] Its preparation steps are as follows:

[0063] Into a dry and clean reaction vessel, add 1mmol phenol, 2mmol CF 3 SO 2 Cl, 2 mL of MeCN, 2 mmol K 2 HPO 4 , while adding 0.05mmol of acridinium salt Under white light irradiation, stir for 24h.

[0064] After the reaction was completed, the reaction was also poured into water, extracted with ethyl acetate, and extracted three times repeatedly, the organic phases were combined, dried over anhydrous sodium sulfate, and the organic phase was concentrated to obtain a crude product, which was separated by column chromatography to obtain a purified product. The product was colorless Liquid, 87% yield.

[0065] Correlation characterization analysis, the results are: 13C NMR (CDCl3, 200MHz, ppm) delta 157.8, 127.3, 123.9 (q, 1J ...

Embodiment 2

[0068] This example provides a preparation method of 1,4-dimethoxy-2-trifluoromethyl-benzene. The structural formula of the 1,4-dimethoxy-2-trifluoromethyl-benzene is shown in the following molecular structural formula I2:

[0069]

[0070] Its preparation process is as follows:

[0071] Into a dry and clean reaction vessel, add 1mmol 1,4-dimethoxybenzene, 4mmol CF 3 SO 2 Cl, 2 mL of MeCN, 2 mmol K 2 HPO 4 , while adding 0.05mmol of ruthenium catalyst Under white light irradiation, stir for 36h.

[0072] After the reaction, the reaction solution was poured into water, extracted with ethyl acetate, and extracted three times, the organic phase was combined, dried over anhydrous sodium sulfate, and the organic phase was concentrated to obtain a crude product, which was subjected to column chromatography to obtain a purified product , the product was a white solid with a yield of 79%.

[0073] The product I2 prepared is subjected to characterization data analysis, and t...

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Abstract

The invention discloses a preparation method and application of an aryl trifluoromethyl compound. The preparation method comprises the step of reacting a compound A with a trifluoromethyl reagent in an organic solvent system containing a catalyst under the illumination and alkaling conditions to obtain the aryl trifluoromethyl compound. The structural formula of the compound A is shown as the follows: A (the formula is shown in the description). The R in the structural formula of the compound A is one or more than two of alkyl, alkoxy, hydroxy, halogen, nitryl and carboxyl. The preparation method disclosed by the invention has the advantages that reaction conditions are simple; the aryl trifluoromethyl compound can be obtained by reaction raw materials under the action of the illumination,the alkaling conditions and the catalyst; no ligand or precursor compound is needed in the preparation process; a product has catalyst residues.

Description

technical field [0001] The invention belongs to the technical field of synthesis of trifluoromethyl compounds, and in particular relates to a preparation method and application of aryl trifluoromethyl compounds. Background technique [0002] Aromatic trifluoromethyl compounds are an important class of fluorine-containing organic compounds, which can be widely used in pesticides, medicines, functional materials and dyes. Traditional build CF 3 The methods include the use of transition metal copper or palladium complexes for catalysis, and the use of specific functional groups as activating groups. Although great progress has been made in recent years, there are still the following defects: copper or palladium remains in drug synthesis; ligands and excessive and expensive trifluoromethyl reagents are required; precursors for functionalization are required. Body compounds (such as halogenated aromatic hydrocarbons, aryl boronic acids, etc.). [0003] Therefore, we urgently n...

Claims

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Application Information

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IPC IPC(8): C07C39/24C07C37/11C07C41/30C07C43/225C07D213/81C07D231/12C07D265/18C07C213/00C07C217/48
CPCC07C37/11C07C41/30C07C213/00C07D213/81C07D231/12C07D265/18C07C39/24C07C43/225C07C217/48
Inventor 丁小妹韩珂珩周海鹏韩辉张强王雷锋张健叶黄湧
Owner 深圳蓝新科技有限公司
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