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A kind of synthetic method of trifluoromethylated arene

A technology for the synthesis of trifluoromethylated aromatics and a synthesis method, which is applied in the field of synthesis of trifluoromethylated aromatics, can solve the problems of unavailable and expensive, and achieve cheap raw materials, high universality, and good repeatability Effect

Inactive Publication Date: 2016-03-30
FUQING BRANCH OF FUJIAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of the above-mentioned trifluoromethylation reagents have some limitations in large-scale preparation, and are expensive and difficult to obtain industrially.

Method used

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  • A kind of synthetic method of trifluoromethylated arene
  • A kind of synthetic method of trifluoromethylated arene
  • A kind of synthetic method of trifluoromethylated arene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Embodiment 1: preparation compound 2

[0018] Under nitrogen protection, bromoarene compound 1 (2.0 mmol), copper powder (20.0 mmol), elemental iodine (20.0 mmol), trifluoroacetic anhydride ( 20.0mmol, about 2.82mL), N,N-dimethylformamide (10.0mL) and pyridine (5.0mL), sealed and heated to 180°C, and reacted for 12 hours. After the reaction, it was naturally cooled to room temperature. Slowly pour the reaction mixture into 100mL saturated aqueous sodium bicarbonate solution to quench, extract with 100mL ether, repeat the ether extraction three times, combine the organic phases, wash the organic phase once with distilled water, wash once with saturated saline, dry over anhydrous sodium sulfate, filter the organic phase Phase, diethyl ether solvent was distilled off under reduced pressure by a rotary evaporator to obtain a concentrated organic mixture product. The product was further purified by silica gel column chromatography, adsorbent: 300-400 mesh silica gel, eluen...

Embodiment 2

[0024] Embodiment 2: preparation compound 4

[0025] The preparation method was basically the same as in Example 1, except that the bromoarene compound 1 in Example 1 was replaced with the bromoarene compound 3 to obtain 0.320 g of compound 4 as a colorless solid (yield: 72%).

[0026]

[0027] The structural confirmation data of this product are as follows:

[0028] Mass Spectrum: MS(EI):m / z(%)222(100),(M + ).

[0029] H NMR spectrum: 1 HNMR (300MHz, CDCl 3 )δ(ppm):δ=7.68(s,4H),7.61-7.58(m,2H),7.49-7.40(m,3H).

[0030] NMR fluorine spectrum: 19 FNMR (282MHz, CDCl 3 )δ(ppm):δ=-62.3(s,3F).

Embodiment 3

[0031] Embodiment 3: preparation compound 6

[0032] The preparation method was basically the same as in Example 1, except that the bromoarene compound 1 in Example 1 was replaced with the bromoarene compound 5 to obtain 0.278 g of compound 6 as a colorless solid (yield: 71%).

[0033]

[0034] The structural confirmation data of this product are as follows:

[0035] Mass Spectrum: MS(EI):m / z(%)196(100),(M + ).

[0036] H NMR spectrum: 1 HNMR (300MHz, CDCl 3 )δ(ppm):δ=8.16(s,1H),7.97-7.90(m,3H),7.67-7.58(m,3H).

[0037] NMR fluorine spectrum: 19 FNMR (282MHz, CDCl 3 )δ(ppm):δ=-62.2(s,3F).

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Abstract

The invention provides a method for synthesizing trifluoromethylated aromatics. Under the protection of an inert atmosphere, halogenated aromatics, copper powder, elemental iodine and trifluoroacetic anhydride react in an organic solvent to prepare trifluoromethylated Aromatics. The invention has the advantages of simplicity and high efficiency, cheap raw materials, low synthesis cost, universal applicability and high repeatability, and can be extended and applied to the synthesis of other trifluoromethyl aromatic derivatives.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a synthesis method of trifluoromethylated arene. Background technique [0002] Trifluoromethyl group is an important class of fluorine-containing groups. Compounds containing trifluoromethyl groups have special physical and chemical properties, and are widely used in the fields of medicine, pesticides and materials. Especially in the field of medicine, compared with ordinary molecules without fluorine, drug molecules containing trifluoromethyl can more easily pass through the cell membrane, thus having better bioavailability. In addition, trifluoromethyl has excellent lipophilic properties, introducing it into the drug matrix can significantly increase the lipid solubility of drug molecules, thereby improving the drug’s ability to penetrate cell membranes, and even better cross the blood-brain barrier , to achieve a better therapeutic effect. For example, trifluor...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C22/08C07C17/32C07C205/11C07C201/12C07D333/54C07D235/10C07D209/10C07D263/56
Inventor 卢修强陈盛叶瑞洪陈玉成刘华
Owner FUQING BRANCH OF FUJIAN NORMAL UNIV