7500-37-0

Usage

Synthesis Reference(s)

Synthetic Communications, 16, p. 1777, 1986 DOI: 10.1080/00397918608057200

InChI:InChI=1/C10H9BrO3/c1-7(12)14-6-10(13)8-2-4-9(11)5-3-8/h2-5H,6H2,1H3

Upstream product

• 4203-30-9 1-(4-bromo-phenyl)-2-diazo-ethanone 
• 64-19-7 acetic acid 
• 127-09-3 sodium acetate 
• 99-73-0 para-bromophenacyl bromide 
• 628-52-4 chromium(II) acetate 
• 60488-44-0 2-dodecyl-5-methyl-resorcinol monomethyl ether 
• 127-08-2 potassium acetate 
• 10534-59-5 tetrabutylammonium acetate 
• 56-36-0 tributyltin acetate 
• 882766-90-7 7-methoxy-4-methyl-3,4-dihydrocoumarin 
• 4209-02-3 1-(4-bromophenyl)-2-chloroethan-1-one 
• 99-90-1 para-bromoacetophenone 
• 108-24-7 acetic anhydride 
• 108-86-1 bromobenzene 

Downstream Products

• 83081-06-5 2-(4-Bromo-phenyl)-4-methyl-morpholine 
• 83081-11-2 2-(4-Bromphenyl)-4-butylmorpholin 
• 83081-09-8 2-(4-Bromphenyl)-4-ethylmorpholin 
• 3343-45-1 4-bromo-2-hydroxyacetophenone 
• 306763-43-9 (R)-2-hydroxy-2-(4-bromophenyl)ethyl acetate 
• 306282-43-9 (S)-2-methylcarbonyloxy-1-(4-bromophenyl)ethyl acetate 
• 92093-23-7 1-(4-bromophenyl)ethane-1,2-diol 
• 924899-55-8 C₁₈H₁₄BrNO₃ 
• 22091-49-2 4-(4-bromophenyl)-2-methyloxazole 
• 160332-70-7 (S)-(+)-1-(4-bromophenyl)-1,2-ethanediol 
• 92093-23-7 (R)-(-)-1-(4-bromophenyl)-1,2-ethanediol 
• 99-90-1 para-bromoacetophenone 

Relevant academic research and scientific papers

Influence of Steric Effect on the Pseudo-Multicomponent Synthesis of N-Aroylmethyl-4-Arylimidazoles

A pseudo-three-component synthesis of N-aroylmethylimidazoles 3 with three new C–N bonds formed regioselectively under microwave conditions was developed. Products were obtained by reacting two equivalents of aroylmethyl bromide (ArCOCH2 Br, 1) with the appropriate amidine salt (RCN2 H3.HX, 2) and with K2 CO3 as a base in acetonitrile. The bicomponent reaction also occurred, giving the expected 4(5)-aryl-1H-imidazoles 4. Notably, the ratio of products 3 and 4 is governed by steric factors of the amidine 2 (i.e., R = H, CH3, Ph). Therefore, a computational study was carried out to understand the reaction course regarding product ratio (3/4), regioselectivity, and the steric effects of the amidine substituent group.

Decarboxylative Oxyacyloxylation of Propiolic Acids: Construction of Alkynyl-Containing α-Acyloxy Ketones

Novel decarboxylative oxyacyloxylation of propiolic acids has been developed. This reaction provides an efficient access to alkynyl-containing α-acyloxy ketones from readily available starting materials and exhibits significant functional group tolerance. Furthermore, oxyacyloxylation of terminal alkynes and aliphatic propiolic acids was also developed. A possible reaction mechanism is proposed based on mechanistic studies.

Metal-Free Amidation Reactions of Terminal Alkynes with Benzenesulfonamide

A novel and efficient approach has been developed to synthesize α-sulfonylamino ketones through the reaction between terminal alkynes and sulfonamides under ambient air using PIDA (diacetoxy iodobenzene). A library of α-sulfonylamino ketone derivatives having a variety of substituents has been synthesized. A plausible reaction pathway has been predicted. This reaction offers a broad substrate scope, metal-free synthesis, excellent regioselectivity, easily accessible reactants, and room temperature reaction conditions under ambient air and is operationally simple. A gram-scale synthesis demonstrates the potential applications of the present method. In addition, we have also synthesized α-acetoxy ketones in the case of absence of sulfonamide.

Imidazolium-Based Ionic Network as a Robust Heterogeneous Catalyst in Synthesis of Phenacyl Derivatives

A new imidazolium-based poly(ionic liquid) has been synthesized and used as a robust heterogeneous catalyst for the preparation of phenacyl derivatives by an SN2 reaction of different phenacyl bromides with a broad range of nucleophiles. The products are obtained in high yields under mild conditions. The catalyst can be recycled efficiently.

Amino propylene glycol derivatives, its preparation method and its pharmaceutical composition and use thereof

The invention discloses a class of amino propanediol derivatives, a preparation method, drug compositions and uses thereof, and particularly relates to a class of new immunoloregulation agents represented by a general formula (I), a preparation method, drug compositions containing the immunoloregulation agents, and especially uses of the immunoloregulation agents as immunoloregulation drugs. The compound with characteristics of excellent treatment effect and low toxicity can be used in the fields of immunologic derangement and immunosuppression, and can further be used for treatment of hypoimmunity, organ transplant rejection and autoimmune diseases. The formula I is defined in the instruction.

PhI(OAc)2-promoted umpolung acetoxylation of enamides for the synthesis of α-acetoxy ketones

Umpolung is a fundamental concept in organic chemistry, which provides an alternative strategy for the synthesis of target compounds which were not easily accessible by conventional methods. Herein, a mild and efficient PhI(OAc)2-promoted umpolung acetoxylation reactions of enamides was developed for the synthesis of α-acetoxy ketones. The reaction tolerates a wide range of functional groups and affords α-acetoxy ketones in good to excellent yields. PhI(OAc)2 serves as a source of acetoxy in the reaction.

Integration of aqueous biphasic with magnetically recyclable systems: Polyethylene glycol-grafted Fe3O4 nanoparticles catalyzed phenacyl synthesis in water

The present work trends to define an efficient phenacyl catalytic synthesis method employing a new nano-magnetite-supported organocatalyst. Polyethylene glycol (PEG) was bonded successfully onto silica coated ferrite and the resultant nanoparticles (PEG@SiO2@Fe3O4) characterized by fourier transform infrared spectroscopy (FT-IR), atomic force microscopy (AFM), thermal gravimetric analysis (TGA), vibrating sample magnetometry (VSM), energy dispersive X-ray analysis (EDAX) and X-ray diffraction (XRD) that exhibited a good catalytic activity in the reaction. The nanoparticles could be easily separated from the reaction mixture by an external magnet and reused in seven reaction cycles without significant loss of activity.

Novel and efficient transformation of enamides into α-acyloxy ketones via an acyl intramolecular migration process

Hydrogen peroxide and anhydride mediated transformation of enamides to afford substituted α-acyloxy ketones is described. This transition-metal-free cascade reaction has a broad substrate scope and high efficiency. The acyl intramolecular migration procedure successfully achieved this acyloxylation process under mild conditions and increased the atom efficiency.

Iron-Catalyzed Dioxygenation of Alkenes and Terminal Alkynes by using (Diacetoxyiodo)benzene as Oxidant

An iron-catalyzed syn-diacetoxylation of alkenes and 1,2-oxyacetoxylation of terminal alkynes has been developed using (diacetoxyiodo)benzene as oxidant. A broad range of internal and terminal alkenes, including electron-rich as well as electron-deficient alkenes, gave the desired products in good to excellent yields with high diastereoselectivity (up to >99:1 dr). In addition the high catalytic activity of iron catalysis for the 1,2-oxyacetoxylation of terminal alkynes is also reported. The roles of catalyst, oxidant and other reaction parameters were evaluated for activation of the unsaturated bond.

Synthesis, characterization and application of β-cyclodextrin-silica nanocomposite as potential microvessel in nucleophilic substitution reaction of phenacyl halides

In the present study, β-cyclodextrin-silica hybrid is synthesized as a novel, efficient and eco-friendly microvessel and solid-liquid phase-transfer catalyst. This molecular host system was applied for nucleophilic substitution reaction of phenacyl halide