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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  • Summary
  • 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 compo

Method used

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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

Examples

Experimental program
Comparison scheme
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Example Embodiment

[0032] The embodiment of the present invention provides a method for preparing an aryltrifluoromethyl compound, which at least includes the following steps:

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

[0034] The structural formula of the 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 aryltrifluoromethyl compound of the present invention will be further explained in detail below.

[0038] In the illumination conditions of the present invention, the preferred wavelength of the light wave is 430nm-550nm. Under the light wave of this wavelength, the catalysis of the transition metal copper or palladium complex can be eliminated, and there is no need to use specific fun...

Example Embodiment

[0059] Example 1

[0060] This embodiment provides a method for preparing 4-trifluoromethylphenol. The structural formula of the 4-trifluoromethylphenol is shown in the following molecular structure I1:

[0061]

[0062] The preparation steps are as follows:

[0063] Add 1mmol phenol and 2mmol CF to a dry and clean reaction vessel 3 SO 2 Cl, 2mL of MeCN, 2mmolK 2 HPO 4 , And add 0.05mmol of acridine salt at the same time Under white light irradiation, stir for 24h.

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

[0065] Related characterization analysis, the result is: 13C NMR (CDCl3, 200MHz, ppm) delta 157.8, 127.3, 123.9 (q, 1J =...

Example Embodiment

[0067] Example 2

[0068] This embodiment provides a method for preparing 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] The preparation process is as follows:

[0071] Add 1mmol 1,4-dimethoxybenzene and 4mmol CF to a dry and clean reaction vessel 3 SO 2 Cl, 2mL of MeCN, 2mmol 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 phases were combined, dried over anhydrous sodium sulfate, and the organic phases were concentrated to obtain a crude product. The crude product was separated by column chromatography to obtain a purified product. The product was a white solid, and the yield was 79%.

[0073] The prepared product I2 is analyzed for characterization d...

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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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