403-30-5

Upstream product

• 108-86-1 bromobenzene 
• 1514-42-7 fluoroacetyl fluoride 
• 359-06-8 monofluoroacetyl chloride 
• 99-73-0 para-bromophenacyl bromide 
• 173974-85-1 N-(1-4'-bromophenylethylidene)-n-butylamine 
• 4203-30-9 1-(4-bromo-phenyl)-2-diazo-ethanone 
• 1046785-17-4 1-bromo-4-(2-fluoro-1,1-dimethoxyethyl)benzene 
• 2039-82-9 1-bromo-4-ethenyl-benzene 
• 364340-35-2 STK₀₈₈₀₄₅ 
• 1374152-33-6 1-(1-azido-2-iodoethyl)-4-bromobenzene 
• 89108-50-9 1-(1-azidovinyl)-4-bromobenzene 
• 64929-35-7 3-(4-bromophenyl)-3-oxopropanoic acid 
• 373-53-5 fluoroiodomethane 
• 192436-83-2 4-bromo-N-methoxy-N-methylbenzamide 

Downstream Products

• 99-90-1 para-bromoacetophenone 
• 156335-24-9 (+/-)-1-(4-bromophenyl)-2-fluoroethanol 
• 7604-31-1 1-(4-bromo-phenyl)-2-fluoro-ethanone-(2,4-dinitro-phenylhydrazone) 
• 201206-41-9 2-bromo-1-(4-bromophenyl)-2-fluoroethan-1-one 
• 343564-26-1 1-(4-bromophenyl)-2,4,4,4-tetrafluoro-1,3-butanedione 
• 1246567-29-2 (±)-1-(4-bromophenyl)-2-fluoro-ethanamine 
• 1246567-42-9 (S)-1-(4-bromophenyl)-2-fluoroethylamine 
• 1246567-36-1 (R)-1-(4-bromophenyl)-2-fluoroethylamine 

Relevant academic research and scientific papers

Method for synthesizing alpha-fluorinated ketone through hydrazone aliphatic chain monoketone

The invention belongs to the technical field of organic synthesis, and provides a method for synthesizing alpha-ketone fluoride through hydrazone aliphatic chain monoketone, which comprises the following steps of: reacting aliphatic chain monoketone with hydrazine hydrate to obtain hydrazone, and reacting hydrazone with a compound represented by formula 2 under a heating condition to complete hydrazone defluorination. The fluorinated product is widely applied to medicines, the reaction conditions are mild, and the process is simple.

Unbalanced-Ion-Pair-Catalyzed Nucleophilic Fluorination Using Potassium Fluoride

An unbalanced ion pair promoter (e.g., tetrabutylammonium sulfate), consisting of a bulky and charge-delocalized cation and a small and charge-localized anion, greatly accelerates nucleophilic fluorinations using easy handling KF. We also successfully converted an inexpensive and commercially available ion-exchange resin to the polymer-supported ion pair promoter (A26–SO42–), which could be reused after filtration. Moreover, A26–SO42– can be used in continuous flow conditions. In our conditions, water is well-tolerated.

Double Enzyme-Catalyzed One-Pot Synthesis of Enantiocomplementary Vicinal Fluoro Alcohols

A double-enzyme-catalyzed strategy for the synthesis of enantiocomplementary vicinal fluoro alcohols through a one-pot, three-step process including lipase-catalyzed hydrolysis, spontaneous decarboxylative fluorination, and subsequent ketoreductase-catalyzed reduction was developed. With this approach, β-ketonic esters were converted to the corresponding vicinal fluoro alcohols with high isolated yields (up to 92percent) and stereoselectivities (up to 99percent). This new cascade process addresses some issues in comparison with traditional methods such as environmentally hazardous reaction conditions and low stereoselectivity outcome.

Fluoro-Substituted Methyllithium Chemistry: External Quenching Method Using Flow Microreactors

The external quenching method based on flow microreactors allows the generation and use of short-lived fluoro-substituted methyllithium reagents, such as fluoromethyllithium, fluoroiodomethyllithium, and fluoroiodostannylmethyllithium. Highly chemoselective reactions have been developed, opening new opportunities in the synthesis of fluorinated molecules using fluorinated organometallics.

Decarboxylative fluorination of β-Ketoacids with N-fluorobenzenesulfonimide (NFSI) for the synthesis of α-fluoroketones: Substrate scope and mechanistic investigation

Cesium carbonate (Cs2CO3)-mediated decarboxylative fluorination of β-ketoacids using NFSI in the MeCN/H2O mixed solvent system affords α-fluoroketones with a broad scope. Both electron-rich and electron-deficient α-non-substituted β-ketoacids are amenable to this protocol. The mechanistic study indicates that the reaction proceeds through electrophilic fluorination followed by decarboxylation, which is different from the decarboxylative fluorination of normal carboxylic acids.

Synthesis of α-Fluoroketones from Vinyl Azides and Mechanism Interrogation

An efficient and mild fluorination of vinyl azides for the synthesis of α-fluoroketones is described. The mechanistic studies indicated that a single-electron transfer (SET) and a subsequent fluorine atom transfer process could be involved in the reaction.

Catalytic Promiscuity of Transaminases: Preparation of Enantioenriched β-Fluoroamines by Formal Tandem Hydrodefluorination/Deamination

Transaminases are valuable enzymes for industrial biocatalysis and enable the preparation of optically pure amines. For these transformations they require either an amine donor (amination of ketones) or an amine acceptor (deamination of racemic amines). Herein transaminases are shown to react with aromatic β-fluoroamines, thus leading to simultaneous enantioselective dehalogenation and deamination to form the corresponding acetophenone derivatives in the absence of an amine acceptor. A series of racemic β-fluoroamines was resolved in a kinetic resolution by tandem hydrodefluorination/deamination, thus giving the corresponding amines with up to greater than 99 % ee. This protocol is the first example of exploiting the catalytic promiscuity of transaminases as a tool for novel transformations.

One-Pot Synthesis of α-Fluoroketones and 3-Fluoro-2,4-diaryl-furans from Trifluoromethyl β-Diketones via Decarboxylation

A facile and mild one-pot protocol via decarboxylation of trifluoromethyl β-diketones has been developed for the construction of α-fluoroketones and 3-fluoro-2,4-diarylfurans which are important units in many biologically active compounds and useful precursors in a variety of functional-group transformations.

Metal-free, efficient oxyfluorination of olefins for the synthesis of α-fluoroketones

A novel oxyfluorination of olefin reactions has been developed. The reactions involve a metal-free and green catalytic system for the synthesis of α-fluoroketones which is an important building block for organic synthesis. Moreover, this reaction system exhibits great functional group tolerance.

Synthesis of enantiopure fluorohydrins using alcohol dehydrogenases at high substrate concentrations

The use of purified and overexpressed alcohol dehydrogenases to synthesize enantiopure fluorinated alcohols is shown. When the bioreductions were performed with ADH-A from Rhodococcus ruber overexpressed in E. coli, no external cofactor was necessary to obtain the enantiopure (R)-derivatives. Employing Lactobacillus brevis ADH, it was possible to achieve the synthesis of enantiopure (S)-fluorohydrins at a 0.5 M substrate concentration. Furthermore, due to the activated character of these substrates, a huge excess of the hydrogen donor was not necessary.