219554-67-3

Upstream product

• 2028-81-1 4-methoxybenzenediazonium bromide 
• 140-88-5 ethyl acrylate 
• 104-94-9 4-methoxy-aniline 
• 36600-75-6 2-(4-methoxy-benzyl)-3-oxo-butyric acid ethyl ester 
• 120506-39-0 (4-(bromomethyl)phenoxy) (tert-butyl) dimethylsilane 
• 105-13-5 4-Methoxybenzyl alcohol 
• 623-73-4 diazoacetic acid ethyl ester 
• 2746-25-0 p-Methoxybenzyl bromide 

Downstream Products

• 61924-67-2 ethyl 2-nitro-3-(4-methoxyphenyl)propionate 

Relevant academic research and scientific papers

Homologation of Electron-Rich Benzyl Bromide Derivatives via Diazo C-C Bond Insertion

The ability to manipulate C-C bonds for selective chemical transformations is challenging and represents a growing area of research. Here, we report a formal insertion of diazo compounds into the "unactivated"C-C bond of benzyl bromide derivatives catalyzed by a simple Lewis acid. The homologation reaction proceeds via the intermediacy of a phenonium ion, and the products contain benzylic quaternary centers and an alkyl bromide amenable to further derivatization. Computational analysis provides critical insight into the reaction mechanism, in particular the key selectivity-determining step.

Visible-Light-Induced Intermolecular Dearomative Cyclization of 2-Bromo-1,3-dicarbonyl Compounds and Alkynes: Synthesis of Spiro[4.5]deca-1,6,9-trien-8-ones

A visible-light-induced photocatalytic intermolecular dearomative cyclization of 2-bromo-1,3-dicarbonyl compounds and alkynes afforded biologically important spirocarbocycle structures in moderate to good yields via a 5-exo-dig radical cyclization under mild reaction conditions. A 5.0 mmol scale dearomatization reaction proceeded smoothly with 95% yield even when the catalyst loading was reduced to 0.1 mol %, suggesting that this method was suitable for large-scale synthesis.

Synthesis of heterocycles from arylation products of unsaturated compounds: XIII. 5-R1-benzyl-2-(R2-2-pyridylimino)thiazolidin-4-ones

Meerwein reactions of arenediazonium bromides with methyl and ethyl acrylates gave 3-aryl-2-bromopropionic acid esters which were subjected to cyclocondensation with N-(2-pyridyl)- and N-(6-methyl-2-pyridyl) thioureas to obtain 5-R1-benzyl-2-(R

Synthesis of heterocycles on the basis of arylation products of unsaturated compounds. 11.1 5-R-benzyl-2-iminoselenazolidin-4-ones from ethyl 3-aryl-2-bromopropanoates

Ethyl 3-aryl-2-bromopropanoates 2a-p were prepared by reaction of ethyl acrylate with arenediazonium bromides 1a-p in the presence of CuBr (Meerwein arylation). These compounds react with selenourea to form 5-R-benzyl-2- iminoselenazolidin-4-ones 4a-p. Compounds 4a-p hydrolyze into the corresponding selenazolidin-2,4-diones.

Synthesis of heterocycles from products of the anion arylation of unsaturated compounds. 3. 2-Arylimino-5-arylmethyl-4-thiazolidones

The reaction of esters of 3-aryl-2-bromopropionic acids with N-arylthioureas gives 2-arylimino-5-arylmethyl-4-thiazolidones, which exist in solution as (E) and (Z) isomers of the imino form. 1998 Plenum Publishing Corporation.