20849-77-8

Upstream product

• 2550-26-7 4-Phenyl-2-butanone 
• 130200-27-0 ethyl 2-benzyl-2-chloro-3-oxobutanoate 
• 1560-06-1 1-phenyl-2-butene 
• 78-94-4 methyl vinyl ketone 
• 100-56-1 phenylmercury(II) chloride 
• 53973-14-1 (Z)-3-chloro-4-phenyl-3-buten-2-one 
• 1896-62-4 (E)-benzalacetone 
• 52755-38-1 1-phenyl-2-buten-1-ol 
• 2344-70-9 1-phenyl-3-butanol 
• 36004-04-3 ethyl (E)-1-phenylbut-1-en-3-ol 
• 87769-52-6 tert-butyl 2-benzylacetoacetate 
• 620-79-1 Ethyl 2-benzylacetoacetate 
• 24251-72-7 (1-Benzyl-1-chloro-2-oxo-propyl)-triphenyl-phosphonium; chloride 

Downstream Products

• 65304-56-5 3-phenoxy-4-phenyl-butan-2-one 
• 1896-62-4 (E)-benzalacetone 
• 92099-57-5 3-Chlor-2-methyl-4-phenyl-butanol-⁽²⁾ 
• 61363-88-0 4-Phenyl-3-acetylmercapto-2-butanon 
• 95739-63-2 2-chloro-3,3-difluoro-1-phenylbutane 
• 1821-12-1 4-Phenylbutyric acid 
• 1311386-54-5 4-chloro-3-methyl-1,5-diphenylpent-1-yn-3-ol 
• 1313617-93-4 3-chloro-4-phenylbutan-2-one oxime 

Relevant academic research and scientific papers

Synthesis and reactivity of α-sulfenyl-β-chloroenones, including oxidation and Stille cross-coupling to form chalcone derivatives

The synthesis of a range of novel α-sulfenyl-β-chloroenones from the corresponding α-sulfenylketones, via a NCS mediated chlorination cascade, is described. The scope of the reaction has been investigated and compounds bearing alkyl- and arylthio substituents have been synthesised. In most instances, the Z α-sulfenyl-β-chloroenones were formed as the major products, while variation of the substituent at the β-carbon position led to an alteration in stereoselectivity. Stille cross-coupling with the Z α-sulfenyl-β-chloroenones led to selective formation of Z sulfenyl chalcones, while the E α-sulfenyl-β-chloroenones did not react under the same conditions. Oxidation of the Z α-sulfenyl-β-chloroenones was followed by isomerisation, leading to the E α-sulfinyl-β-chloroenones. Stille cross-coupling with the E α-sulfinyl-β-chloroenones produced the E sulfinyl chalcones. Either the E or Z sulfinyl chalcones can be obtained by altering the sequence of oxidation and Stille cross-coupling.

A Simple and Efficient Method for the Preparation of α-Halogenated Ketones Using Iron(III) Chloride and Iron(III) Bromide as Halogen Sources with Phenyliodonium Diacetate as Oxidant

α-Halogenated ketones are both unique structure moieties existing in biologically natural products and valuable synthetic intermediates for the preparation of functional molecules. An efficient and scalable method for the preparation of α-halogenated ketone using iron (III) chloride and iron (III) bromide as halogen sources with phenyliodonium diacetate as oxidant has been developed, featuring mild reaction conditions, environmentally friendly reagents, and wide substrate scope. Notably, the three-step synthesis of drug prasugrel was achieved using this developed method as a key step with 30% yield on gram-scale. Additionally, the reaction mechanism involving chloride cation was proposed based on some preliminary control experiments. (Figure presented.).

Acid- and iridium-catalyzed tandem 1,3-transposition/3,1-hydrogen shift/chlorination of allylic alcohols

A method for the selective synthesis of α-chlorocarbonyls from allylic alcohols is presented. The reaction occurs through an acid- and iridium-catalyzed tandem process that combines a 1,3-transposition, a 3,1-hydrogen shift, and a chlorination process, and can be applied to a wide range of α-aromatic and heteroaromatic secondary allylic alcohols. Saturated non-chlorinated ketones or other side-products derived from overchlorination were not detected.

Direct conversion of alcohols to α-chloro aldehydes and α-chloro ketones

Direct conversion of primary and secondary alcohols into the corresponding α-chloro aldehydes and α-chloro ketones using trichloroisocyanuric acid, serving both as stoichiometric oxidant and α-halogenating reagent, is reported. For primary alcohols, TEMPO has to be added as an oxidation catalyst, and for the transformation of secondary alcohols (TEMPO-free protocol), MeOH as an additive is essential to promote chlorination of the intermediary ketones.

Enhancements of enantio and diastereoselectivities in reduction of (Z)-3-halo-4-phenyl-3-buten-2-one mediated by microorganisms in ionic liquid/water biphasic system

Reductions of (Z)-C6H5CHCXC(O)CH3 (X = Cl, Br) mediated by Saccharomyces cerevisiae, Candida albicans, Rhodotorula glutinis, Geotrichum candidum and Micrococcus luteus gave the corresponding halohydrins through consecutive

Iridium-catalyzed 1,3-hydrogen shift/chlorination of allylic alcohols

Tandem: Allylic alcohols react with N-chlorosuccinimide (NCS) in a tandem 1,3-H shift/C-Cl bond formation leading to α-chloroketones and α-chloroaldehydes. The reactions proceed with complete selectivity to give single constitutional isomers of monochlorinated carbonyl compounds. The utility of the transformation is illustrated by the straightforward synthesis of 4,5-disubstituted 2-aminothiazoles from allylic alcohols. Copyright

Hydride transfer versus electron transfer in the reduction of 4-phenyl-3-halo-3-buten-2-ones mediated by Pichia stipitis

Reductions of (Z)-C6H5CHCXC(O)CH3 (X = Cl, Br) mediated by Pichia stipitis gave 4-phenylbutan-2-one through dehalogenation of intermediaries 3-halo-4-phenylbutan-2-one by an electron transfer mechanism. The addition of 1,3-dinitrobenzene avoids the dehalogenation and thus the corresponding (2S,3S)-halohydrins were obtained in excellent enantiomeric excesses by a hydride transfer mechanism. Irganox 1010 and 1076 were also used to inhibit the electron transfer mechanism. The obtained halohydrins are important chiral building blocks to obtain optically active epoxides and aminoalcohols.

Enantio and diastereoselective addition of phenylacetylene to racemic α-chloroketones

In this report, we have presented the first diastereoselective addition of phenylacetylene to chiral racemic chloroketones. The addition is controlled by the reactivity of the chloroketones that allowed the stereoselective reaction to be performed at -20

THE CHLORINATION OF KETONES USING TRIMETHYLCHLOROSILANE AND DIMETHYLSULFOXIDE WITH BROMIDE ION CATALYSIS

Chlorination using trimethylchlorosilane and dimerthylsulfoxide with bromide ion catalysis afforded almost quantitative yields for 1,3-diphenylacetone, benzoylacetone and propiophenone, and acceptable yields for acetophenone, acetylacetone and cyclohexanone.

A Synthesis of 2-Fluoro-2-alkenes

A three-step method for the synthesis of 2-fluoro-2-alkenes from the parent methyl ketones has been developed.The yields of the sequence are fair, and no contamination of the products by the isomeric 2-fluoro-1-alkenes can be detected.