Synthetic method for trifluoromethyl methylation arene

A technology for trifluoromethylated aromatic hydrocarbons and a synthesis method, which is applied in the field of synthesis of trifluoromethylated aromatic hydrocarbons, can solve the problems of high price and difficulty in obtaining, and achieves high universality, low price of raw materials, and high yield. Effect

Inactive Publication Date: 2014-10-15
FUQING BRANCH OF FUJIAN NORMAL UNIV
View PDF1 Cites 4 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of the above-mentioned trifluoromethylation reagents have some limitatio

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Synthetic method for trifluoromethyl methylation arene
  • Synthetic method for trifluoromethyl methylation arene
  • Synthetic method for trifluoromethyl methylation arene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Embodiment 1: preparation compound 2

[0018] Under the protection of nitrogen, add brominated aromatic compounds successively into a 50 mL pressure-resistant glass reaction sealed tube with a Teflon cock 1 (2.0 mmol), copper powder (20.0 mmol), elemental iodine (20.0 mmol), trifluoroacetic anhydride (20.0 mmol, about 2.82 mL), N,N-dimethylformamide (10.0 mL) and pyridine (5.0 mL ), heated to 180°C after sealing, and reacted for 12 hours. After the reaction, it was naturally cooled to room temperature. The reaction mixture was slowly poured into 100 mL of saturated aqueous sodium bicarbonate solution to quench, extracted with 100 mL of diethyl ether, repeated diethyl ether extraction three times, combined the organic phase, washed once with distilled water and once with saturated brine, dried over anhydrous sodium sulfate, The organic phase was filtered, and the ether solvent was distilled off under reduced pressure by a rotary evaporator to obtain a concentrated or...

Embodiment 2

[0024] Embodiment 2: preparation compound 4

[0025] The preparation method is basically the same as in Example 1, the difference is that the brominated aromatic compound in Example 1 1 Replaced by Brominated Aromatic Compounds 3 , to get the compound 4 Colorless solid 0.320 g (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 H NMR (300 MHz, 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 F NMR (282 MHz, CDCl 3 ) δ (ppm): δ = -62.3 (s, 3F).

Embodiment 3

[0031] Embodiment 3: preparation compound 6

[0032] The preparation method is basically the same as in Example 1, the difference is that the brominated aromatic compound in Example 1 1 Replaced by Brominated Aromatic Compounds 5 , to get the compound 6 Colorless solid 0.278 g (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 H NMR (300 MHz, 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 F NMR (282 MHz, CDCl 3 ) δ (ppm): δ = -62.2 (s, 3F).

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The invention provides a synthetic method for a trifluoromethyl methylation arene. The trifluoromethyl methylation arene is prepared by reacting a halogenated arene, copper powder, elemental iodine and trifluoroacetic anhydride in an organic solvent under an inert atmosphere protection state. The method has the advantages of being simple and efficient, cheap in raw materials, low in synthetic cost, high in universality and repeatability, and the like, and can be popularized and applied to the fields of the synthesis of trifluoromethyl methylation 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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
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
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap