347-84-2

Usage

Uses

Used in Pharmaceutical Industry:
4'-FLUORO-2-PHENYLACETOPHENONE is used as a chemical intermediate for the preparation of 2,3-diarylpyrazines and quinoxalines, which are selective COX-2 inhibitors. These inhibitors play a crucial role in the development of anti-inflammatory and analgesic drugs, as they help reduce inflammation and pain by targeting the specific enzyme responsible for prostaglandin synthesis.
In the synthesis of these compounds, 4'-FLUORO-2-PHENYLACETOPHENONE serves as a building block, providing the necessary structural elements for the formation of the desired molecules. Its presence in the final product contributes to the overall effectiveness and selectivity of the COX-2 inhibitors, making it an essential component in the development of new and improved pharmaceuticals for the treatment of various inflammatory and pain-related conditions.

Upstream product

• 462-06-6 fluorobenzene 
• 103-80-0 phenylacetyl chloride 
• 395-21-1 1-(4-fluorophenyl)-1-phenylethylene 
• 405-29-8 (4-fluorophenyl)phenylacetylene 
• 1600-27-7 mercury(II) diacetate 
• 532-27-4 1-chloroacetophenone 
• 352-13-6 4-flourophenylmagnesium bromide 
• 100-39-0 benzyl bromide 
• 403-43-0 4-fluorobenzoyl chloride 
• 1765-93-1 4-fluoroboronic acid 
• 140-29-4 phenylacetonitrile 
• 437-29-6 tris(4-fluorophenyl)bismuthane 
• 201230-82-2 carbon monoxide 
• 100-44-7 benzyl chloride 

Downstream Products

• 436-02-2 2-(4-fluoro-phenyl)-3-phenyl-quinoline-4-carboxylic acid 
• 73424-43-8 1-(4-Fluorphenyl)-2-phenyl-1-ethanon-p-tolylsulfonylhydrazon 
• 23075-70-9 2-diazo-1-(4-fluorophenyl)-2-phenylethan-1-one 
• 31464-85-4 1-(4-Fluoro-phenyl)-2-{[2-(4-fluoro-phenyl)-2-oxo-1-phenyl-eth-(E)-ylidene]-hydrazono}-2-phenyl-ethanone 
• 88675-31-4 2-bromo-1-(4-fluorophenyl)-2-phenylethan-1-one 
• 185345-82-8 4-[2-(4-fluorophenyl)-2-oxoethyl]-1-benzenesulfonamide 
• 323-28-4 C₁₅H₁₄FN₃O 
• 445411-74-5 benzyl p-fluorophenyl ketoxime 
• 125971-96-2 2-[2-(4-fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxopentanoic acid phenylamide 
• 1407998-19-9 3-(4-(4-fluorophenyl)-5-phenyloxazol-2-yl)propanoic acid 
• 1407998-17-7 methyl 3-(4-(4-fluorophenyl)-5-phenyloxazol-2-yl)propanoate 
• 1448819-68-8 2-(4-fluorophenyl)-1-phenethyl-3-phenyl-1H-pyrrole 
• 1428476-54-3 (R)-2-(4-fluorophenyl)-4-methyl-1-phenylpent-4-en-2-ol 
• 1403667-08-2 1,4-bis(4-fluorophenyl)-2,3-diphenylbutane-1,4-dione 

Relevant academic research and scientific papers

Electrochemical oxidation-induced benzyl C–H carbonylation for the synthesis of aromatic α-diketones

Electrochemical oxidation-induced direct carbonylation of benzyl C–H bond for the synthesis of aromatic α-diketones is described. In this process, tetrabutylammonium iodide (nBu4NI) not only acts as an electrolyte, but its iodine anion is oxidized to an iodine radical at the anode, acting as a hydrogen atom transfer agent. The iodine radical extracts the benzyl hydrogen atom and causes the carbonylation of the benzyl position, where O2 in the air is used as an oxygen source.

H2O2-mediated room temperature synthesis of 2-arylacetophenones from arylhydrazines and vinyl azides in water

An environmentally benign, cost-efficient and practical methodology for the room temperature synthesis of 2-arylacetophenones in water has been discovered. The facile and efficient transformation involves the oxidative radical addition of arylhydrazines with α-aryl vinyl azides in the presence of H2O2 (as a radical initiator) and PEG-800 (as a phase-transfer catalyst). From the viewpoint of green chemistry and organic synthesis, the present protocol is of great significance because of using cheap, non-toxic and readily available starting materials and reagents as well as amenability to gram-scale synthesis, which provides an attractive strategy to access 2-arylacetophenones.

METHOD OF PREPARING(3R,5R)-7-(2-(4-FLUOROPHENYL)-5-ISOPROPYL-3-PHENYL-4-((4-HYDROXYMETHYLPHENYLAMINO)CARBONYL)-PYRROL-1-YL)-3,5-DIHYDROXY-HEPTANOIC ACID HEMI CALCIUM SALT, AND METHOD OF PREPARING INTERMEDIATES USED THEREIN

The present invention provides a method for preparing (3R,5R)-7-(2-(4-flurophenyl)-5-isopropyl-3-phenyl-4-((4-hydroxymethylphenylamino)carbonyl)-pyrrole-1-yl)-3,5-dihydroxy heptanoic acid hemicalcium salt. The preparation method of the present invention is performed in a convergent synthesis manner in which main structural moieties of a (3R,5R)-7-(2-(4-flurophenyl)-5-isopropyl-3-phenyl-4-((4-hydroxymethylphenylamino)carbonyl)-pyrrole-1-yl)-3,5-dihydroxy heptanoic acid hemicalcium salt are independently synthesized, and then coupled. Accordingly, related substances can be easily controlled and preparing time can be reduced, thus improving the productivity of a compound, and the yield of a final compound can also be increased.

Benzylic Aroylation of Toluenes Mediated by a LiN(SiMe3)2/Cs+System

Chemoselective deprotonative functionalization of benzylic C-H bonds is challenging, because the arene ring contains multiple aromatic C(sp2)-H bonds, which can be competitively deprotonated and lead to selectivity issues. Recently it was found that bimetallic [MN(SiMe3)2 M = Li, Na]/Cs+ combinations exhibit excellent benzylic selectivity. Herein, is reported the first deprotonative addition of toluenes to Weinreb amides mediated by LiN(SiMe3)2/CsF for the synthesis of a diverse array of 2-arylacetophenones. Surprisingly, simple methyl benzoates also react with toluenes under similar conditions to form 2-arylacetophenones without double addition to give tertiary alcohol products. This finding greatly increases the practicality and impact of this chemistry. Some challenging substrates with respect to benzylic deprotonations, such as fluoro and methoxy substituted toluenes, are selectively transformed to 2-aryl acetophenones. The value of benzylic deprotonation of 3-fluorotoluene is demonstrated by the synthesis of a key intermediate in the preparation of Polmacoxib.

Iron-Catalyzed Enantioselective Radical Carboazidation and Diazidation of α,β-Unsaturated Carbonyl Compounds

Azidation of alkenes is an efficient protocol to synthesize organic azides which are important structural motifs in organic synthesis. Enantioselective radical azidation, as a useful strategy to install a C-N3 bond, remains challenging due to the inherently instability and unique structure of radicals. Here, we disclose an efficient enantioselective radical carboazidation and diazidation of α,β-unsaturated ketones and amides catalyzed by chiral N,N′-dioxide/Fe(OTf)2 complexes. An array of substituted alkenes was transformed to the corresponding α-azido carbonyl derivatives in good to excellent enantioselectivities, benefiting the preparation of chiral α-amino ketones, vicinal amino alcohols, and vicinal diamines. Control experiments and mechanistic studies proved the radical pathway in the reaction process. The DFT calculations showed that the azido transferred to the radical intermediate via an intramolecular five-membered transition state with the internal nitrogen of the Fe-N3 species.

Four-Step Domino Reaction Enables Fully Controlled Non-Statistical Synthesis of Hexaarylbenzene with Six Different Aryl Groups**

Hexaarylbenzene (HAB) derivatives are versatile aromatic systems playing a significant role as chromophores, liquid crystalline materials, molecular receptors, molecular-scale devices, organic light-emitting diodes and candidates for organic electronics. Statistical synthesis of simple symmetrical HABs is known via cyclotrimerization or Diels–Alder reactions. By contrast, the synthesis of more complex, asymmetrical systems, and without involvement of statistical steps, remains an unsolved problem. Here we present a generally applicable synthetic strategy to access asymmetrical HAB via an atom-economical and high-yielding metal-free four-step domino reaction using nitrostyrenes and α,α-dicyanoolefins as easily available starting materials. Resulting domino product—functionalized triarylbenzene (TAB)—can be used as a key starting compound to furnish asymmetrically substituted hexaarylbenzenes in high overall yield and without involvement of statistical steps. This straightforward domino process represents a distinct approach to create diverse and still unexplored HAB scaffolds, containing six different aromatic rings around central benzene core.

Palladium-catalyzed synthesis of α-aryl acetophenones from styryl ethers and aryl diazonium saltsviaregioselective Heck arylation at room temperature

Preparation of α-aryl acetophenones from styryl ethers and aryldiazonium salts is described. The reaction is catalyzed by palladium acetate at room temperature in the absence of ligand and base. The developed method is highly attractive in terms of reaction conditions, substrate scope, functional group tolerance and yields. Synthetic applications of the present method are demonstrated by preparing α-aryl indoles and 3-aryl isocoumarin from styryl ethers.

Ruthenium(II)-Catalyzed Cross-Coupling of Benzoyl Formic Acids with Toluenes: Synthesis of 2-Phenylacetophenones

Herein, we report a direct method to synthesize 2-phenylacetophenone through a ruthenium(II)-catalyzed cross-coupling reaction between acyl and benzyl radical. The various derivatives of 2-phenylacetophenone were prepared easily in moderate to good yields. These reactions provide a straightforward pathway to synthesize a variety of ketones bearing various functional groups.

Versatile and base-free copper-catalyzed α-arylations of aromatic ketones using diaryliodonium salts

A ligand and base-free copper catalyzed synthetic method for the efficient α-arylation of aromatic ketones is described. In order to avoid strong bases, ketone-derived silyl enol ethers were employed. Their reaction with diaryliodonium salts as aryl source provided the intermolecular C–C coupling displaying good functional group tolerance and requiring low catalyst loading.

The organocatalytic enantiodivergent fluorination of β-ketodiaryl-phosphine oxides for the construction of carbon-fluorine quaternary stereocenters

Commercially available cinchona alkaloids that can catalyze the enantiodivergent fluorination of β-ketodiarylphosphine oxides were developed to construct carbon-fluorine quaternary stereocenters. This protocol features a wide scope of substrates and excellent enantioselectivities, and it is scalable.