2251-60-7

Upstream product

• 2251-82-3 1-(difluoromethyl)-4-(trifluoromethyl)benzene 
• 455-19-6 4-Trifluoromethylbenzaldehyde 
• 75-61-6 dibromodifluoromethane 
• 455-13-0 4-Iodobenzotrifluoride 
• 2250-36-4 1-(bromodifluoromethyl)-4-(difluoromethyl)benzene 
• 73790-11-1 α,α-difluoro-4-(trifluoromethyl)benzeneacetic acid 
• 73789-96-5 ethyl α,α-difluoro-4-(trifluoromethyl)benzeneacetate 
• 619-66-9 4-Carboxybenzaldehyde 

Downstream Products

• 114467-78-6 1-(Difluoro-phenylsulfanyl-methyl)-4-trifluoromethyl-benzene 
• 114467-82-2 1-(Difluoro-phenoxy-methyl)-4-trifluoromethyl-benzene 
• 114467-87-7 1-(Azido-difluoro-methyl)-4-trifluoromethyl-benzene 
• 433-19-2 1,4-bis(trifluoromethyl)benzene 

Relevant academic research and scientific papers

Bromodifluoromethylation of aromatic Grignard reagents with CF2Br2

The bromodifluoromethylation of aromatic Grignard reagents having electron-withdrawing groups with dibromodifluoromethane (CF2Br2) was developed. The reaction proceeded to give the corresponding (bromodifluoromethyl)benzene derivatives via a difluorocarbene-mediated mechanism.

Frustrated Lewis-Pair-Meditated Selective Single Fluoride Substitution in Trifluoromethyl Groups

Single fluoride substitution in trifluoromethylarenes is an ongoing synthetic challenge that often leads to "over-reaction", where multiple fluorides are replaced. Development of this reaction would allow simple access to a vast range of difluoromethyl derivatives of current interest to pharmaceutical, agrochemistry, and materials sciences. Using a catalytic frustrated Lewis pair approach, we have developed a generic protocol that allows a single substitution of one fluoride in trifluoromethyl groups with neutral phosphine and pyridine bases. The resulting phosphonium and pyridinium salts can be further functionalized via nucleophilic substitution, photoredox coupling, and electrophilic transfer reactions allowing the generation of a vast array of difluoromethyl products.

Synthesis of trifluoromethyl moieties by late-stage copper (I) mediated nucleophilic fluorination

The nucleophilic fluorination of bromodifluoromethyl derivatives mediated by the complex (PPh3)3CuF is described. Under the reaction conditions, different trifluoroacetates, trifluoroketones, trifluoroarenes and trifluoroacetamides were obtained in good yields.

18F-Labeling of Aryl-SCF3, -OCF3 and -OCHF2 with [18F]Fluoride

We report that halogenophilic silver(I) triflate permits halogen exchange (halex) nucleophilic 18F-fluorination of aryl-OCHFCl, -OCF2Br and -SCF2Br precursors under mild conditions. This AgI-mediated process allows for the first time access to a range of 18F-labeled aryl-OCHF2, -OCF3 and -SCF3 derivatives, inclusive of [18F]riluzole. The 18F-labeling of these medicinally important motifs expands the radiochemical space available for PET applications. A halogen exchange (halex) 18F-fluorination process offers access for the first time to 18F-labeled arylOCF3, arylOCHF2 and arylSCF3, three motifs of established medicinal importance in PET radiotracers. The use of silver(I) triflate is critical to permit 18F-labeling under mild conditions.

(BROMODIFLUOROMETHYL)BENZENE DERIVATIVES AND METHOD OF PRODUCING THEM

PROBLEM TO BE SOLVED: To provide (bromodifluoromethyl)benzene derivatives useful as production intermediates of pharmaceutical/agricultural chemicals and functional materials, and a method of producing them. SOLUTION: An aryl magnesium reagent (Grignard reagent) represented by general formula (1) is reacted with dibromodifluoromethane to produce (bromodifluoromethyl)benzene derivatives. In the formula, R1 is a fluoroalkyl group having 1-6 carbon atoms or the like, R2 is a hydrogen atom or the like, m is an integer of 1-5, n is an integer of 0-4, and X is a halogen atom. COPYRIGHT: (C)2015,JPOandINPIT

Syntheses of New Aromatic Compounds with Fluorinated Side Chains and their Chemical Reactivity

The syntheses of a wide range of aromatic compounds of the type p-Y-C6H4CF2X(4-13) are described, and the chemical behavior of these compounds as a function of substituent Y is investigated .Analogously the pyridine derivatives 15, 17, and 18 were synthesized and characterized.From a correlation of the 19F-NMR data of these compounds with the Hammett constant of Y, participation of C-F ?-back-donation is seen as the cause for an observed shift of the 19F signals to lower field.