250674-72-7

Upstream product

• 106-40-1 4-bromo-aniline 
• 76-05-1 trifluoroacetic acid 

Downstream Products

• 1310569-10-8 N-(4-bromophenyl)-2,2,2-trifluoroethanethioamide 
• 1613146-21-6 1-(4-bromophenyl)-4-(4-methylbenzenesulfonyl)-5-(trifluoromethyl)-1H-imidazole 
• 24568-11-4 N-(4-bromophenyl)-2,2,2-trifluoro-acetamide 

Relevant academic research and scientific papers

Silver-Mediated [3 + 2] Cycloaddition of Azomethine Ylides with Trifluoroacetimidoyl Chlorides for the Synthesis of 5-(Trifluoromethyl)imidazoles

A silver-mediated [3 + 2] cycloaddition of azomethine ylides with trifluoroacetimidoyl chlorides for the rapid assembly of 5-(trifluoromethyl)imidazoles has been developed. Notable features of the reaction include readily accessible reagents, a broad substrate scope, and high efficiency. The protocol can be successfully applied to construct the analogue of the specific allosteric modulator of GABAA receptors. The silver species could be recycled by a simple operation.

Synthesis of 5-Trifluoromethyl-1,2,4-Triazoles via Metal-Free Annulation of Trifluoroacetimidohydrazides and Methyl Ketones

A metal-free approach for the synthesis of 5-trifluoromethyl-1,2,4-triazoles via I2-mediated [4+1] annulation of readily available trifluoroacetimidohydrazides and methyl ketones has been achieved. The transformation involves iodination/Kornblum oxidation, intermolecular dehydration condensation and an iodine-mediated intramolecular cyclization/aromatization sequence. The developed protocol can be easily scaled up to 3 mmol scale without obvious efficiency decrease and be implemented by a consecutive one-pot manner. (Figure presented.).

The cascade coupling/iodoaminocyclization reaction of trifluoroacetimidoyl chlorides and allylamines: metal-free access to 2-trifluoromethyl-imidazolines

A metal-free cascade coupling/iodoaminocyclization reaction for the rapid assembly of 2-trifluoromethyl-imidazolines has been disclosed. The transformation applies readily accessible trifluoroacetimidoyl chlorides, allylamines andN-iodosuccinimides as the starting substrates, achieving an efficient and straightforward pathway to construct diverse imidazoline derivatives. Excellent efficiency of the reaction is observed (higher than 90% isolated yield for half of the examples), and the obtained imidazoline products bearing a pendent iodomethyl group could be easily transformed into other synthetically valuable compounds.

Annulation of CF3-Imidoyl Sulfoxonium Ylides with 1,3-Dicarbonyl Compounds: Access to 1,2,3-Trisubstituted 5-Trifluoromethylpyrroles

A lithium-bromide-promoted nucleophilic substitution/annulation cascade reaction between CF3-imidoyl sulfoxonium ylides and 1,3-dicarbonyl compounds has been established, and the corresponding 1,2,3-trisubstituted 5-trifluoromethylpyrroles have been obtai

Oxidative Cyclization of Trifluoroacetimidohydrazides with D-Glucose for the Metal-Free Synthesis of 3-Trifluoromethyl-1,2,4-Triazoles

A metal-free oxidative cyclization of readily available trifluoroacetimidohydrazides with D-glucose for the assembly of 3-trifluoromethyl-1,2,4-triazoles has been disclosed. D-glucose is applied as C1 synthon to provide methine source in the reaction. Control experiments have been conducted to shed light on the reaction mechanism. The synthetic utility of the protocol has been explored by the implementation of scale up reaction and the synthesis of the key skeleton of NKI-receptor ligand. (Figure presented.).

Palladium-Catalyzed Four-Component Carbonylative Cyclization Reaction of Trifluoroacetimidoyl Chlorides, Propargyl Amines, and Diaryliodonium Salts: Access to Trifluoromethyl-Containing Trisubstituted Imidazoles

A palladium-catalyzed four-component carbonylative cyclization reaction for the expeditious construction of trifluoromethyl-containing trisubstituted imidazoles has been achieved. With readily accessible trifluoroacetimidoyl chlorides, propargyl amines, a

FeCl3-Mediated Synthesis of 2-(Trifluoromethyl)quinazolin-4(3 H)-ones from Isatins and Trifluoroacetimidoyl Chlorides

An FeCl3-mediated cascade coupling/decarbonylative annulation reaction for the efficient construction of 2-(trifluoromethyl)quinazolin-4(3H)-ones has been developed. This transformation employs readily available isatins and trifluoroacetimidoyl chlorides as the starting materials, providing a facile and practical route to diverse biologically relevant quinazolin-4(3H)-one derivatives. A plausible reaction pathway has been proposed based on the mechanistic observations.

A Convenient FeCl3-Mediated Synthesis of 5-Trifluoromethyl-1,2,4-triazoles from Trifluoroacetimidoyl Chlorides and Hydrazides

A low cost FeCl3-mediated cascade annulation of trifluoroacetimidoyl chlorides and hydrazides for the efficient synthesis of 5-trifluoromethyl-1,2,4-triazoles has been developed. The transformation proceeds through a cascade base-promoted intermolecular C?N bond formation and FeCl3-mediated intramolecular dehydration sequence under mild conditions. The protocol exhibits many notable features and can be readily scaled up to gram scale. (Figure presented.).

A simple synthesis of trifluoromethylated pyridinium azomethine ylides by three-component reaction between pyridines, phenacyl bromides, and N-aryltrifluoroacetimidoyl chlorides

[Figure not available: see fulltext.] A novel synthesis of trifluoromethylated pyridinium azomethine ylides by three-component reaction between pyridines, phenacyl bromides, and trifluoromethylated imidoyl chlorides in acetonitrile as solvent at room temperature without any catalyst is described. The FT-IR, 1H, 13C, 19F NMR spectral and elemental analysis confirm the structures of products. The synthesized azomethine ylides are easily purified by washing with diethyl ether and are stable even at high temperature. Heating of these ylides in refluxing acetonitrile, ethanol, or DMSO did not result in the intramolecular cyclization to imidazopyridine derivatives and only starting ylides were isolated.

Preparation of Trifluoromethylated (Arylaminomethylene)malononitriles Suitable for Synthesis of 4-Amino-2-(trifluoromethyl) quinoline Derivatives by Intramolecular Friedel-Crafts Reaction

An approach for the synthesis of 4-amino-2-(trifluoromethyl)quinolines via the intramolecular Friedel-Crafts reaction of 2-(1-(arylamino)-2,2,2-trifluoroethylidene)malononitrile derivatives is reported. This simple protocol provides a wide variety of 4-am