5837-69-4

Upstream product

• 100-42-5 styrene 
• 4254-22-2 acetyl hypobromite 
• 2425-28-7 2-Bromo-1-phenylethanol 
• 75-36-5 acetyl chloride 
• 70-11-1 α-bromoacetophenone 
• 108-24-7 acetic anhydride 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 93-56-1 phenylethane 1,2-diol 
• 64-19-7 acetic acid 
• 127-19-5 N,N-dimethyl acetamide 
• 2425-28-7 (S)-2-bromo-1-phenylethanol 

Downstream Products

• 2206-94-2 1-acetoxy-1-phenylethene 
• 93-92-5 1-phenylethyl acetate 
• 2425-28-7 (S)-2-bromo-1-phenylethanol 
• 73908-24-4 (-)-(R)-2-bromo-1-phenyl-1-acetoxyethane 

Relevant academic research and scientific papers

Zwitterion-Catalyzed Intermolecular Bromoesterifications

Intermolecular haloesterification is an important class of transformations. The resulting products are valuable building blocks. However, it is often necessary to use super-stoichiometric amount of acid in order to compensate the low reactivity. Herein, we report a zwitterion-catalyzed intermolecular bromoesterification using acid and olefin in an equimolar ratio. Mechanistic study revealed that the charge pair in the zwitterion works synergistically in activating both NBS and carboxylic acid.

Lipase mediated enzymatic kinetic resolution of phenylethyl halohydrins acetates: A case of study and rationalization

Racemic phenylethyl halohydrins acetates containing several groups attached to the aromatic ring were resolved via hydrolysis reaction in the presence of lipase B from Candida antarctica (Novozym 435). In all cases, the kinetic resolution was highly selective (E > 200) leading to the corresponding (S)-β-halohydrin with ee > 99 %. However, the time required for an ideal 50 % conversion ranged from 15 min for 2,4-dichlorophenyl chlorohydrin acetate to 216 h for 2-chlorophenyl bromohydrin acetate. Six chlorohydrins and five bromohydrins were evaluated, the latter being less reactive. For the β-brominated substrates, steric hindrance on the aromatic ring played a crucial role, which was not observed for the β-chlorinated derivatives. To shed light on the different reaction rates, docking studies were carried out with all the substrates using MD simulations. The computational data obtained for the β-brominated substrates, based on the parameters analysed such as NAC (near attack conformation), distance between Ser-O and carbonyl-C and oxyanion site stabilization were in agreement with the experimental results. On the other hand, the data obtained for β-chlorinated substrates suggested that physical aspects such as high hydrophobicity or induced change in the conformation of the enzymatic active site are more relevant aspects when compared to steric hindrance effects.

Method for synthesizing beta-bromoacetate compounds

The invention discloses a method for synthesizing beta-bromoacetate compounds. The method comprises the following steps: reacting in an organic solvent at a temperature of 15-60 DEG C for 1-6 hours bytaking styrene compounds shown as a formula I as raw ma

Immobilization of Amano lipase from Pseudomonas fluorescens on silk fibroin spheres: an alternative protocol for the enantioselective synthesis of halohydrins

The search for a new, efficient, cheaper and sustainable matrix for lipase immobilization is a growing area in biotechnology. Amano lipase from Pseudomonas fluorescens was immobilized on silk fibroin spheres and used in the enzymatic kinetic resolution of halohydrins, to obtain optically active epoxides (up to 99% ee), important precursors in the synthesis of derivative antifungal azoles. This paper reinforces the versatility of silk fibroin as a support for heterogeneous catalysts.

Intermolecular Halogenation/Esterification of Alkenes with N-Halosuccinimide and Acetic Acid Catalyzed by 1,4-Diazabicyclo[2.2.2]octane

1,4-Diazabicyclo[2.2.2]octane (DABCO) is a suitable Lewis base that acts as an organocatalyst in the activation of N-chlorosuccinimide (NCS) towards the chlorination of alkenes. The chloriranium ion formed from NCS and the alkene, can be intermolecularly opened by a nucleophile, such as acetic acid, to produce highly functionalized trans-chloro esters in high yields. The protocol is also applied to the synthesis of chlorohydrins and chloro ethers using water or methanol as nucleophiles instead of acetic acid. Brominated analogs can also be synthesized from alkenes and N-bromosuccinimide (NBS) in the presence of various basic catalysts. However, the reaction patterns seem to be remarkably different. The catalytic performance of bases in the bromoesterification of alkenes was found to be strongly affected by their Br?nsted basicity, suggesting that acetyl hypobromite, formed in situ from NBS and acetic acid, acts as a real brominating agent in these systems. (Figure presented.).

A simple and facile method for regio- and stereoselective bromoformyloxylation and bromoacetoxylation of olefins using NH4Br and oxone

A mild and efficient protocol for the preparation of bromoformates as well as bromoacetates from olefins using NH4Br and oxone in nucleophile sources (DMF or DMA) without employing catalyst at room temperature is described. This method is facile, environmentally friendly and cost effective. A variety of terminal, internal and cyclic alkenes reacted smoothly to give the corresponding bromoformate and acetate products in good to excellent yields. Moreover, 1,2-disubstituted olefins provided moderate to excellent diastereoselectivity.

Direct C-H amination of arenes with alkyl azides under rhodium catalysis

New horizons in the utility of azides: The rhodium-catalyzed intermolecular direct C-H amination of arenes with alkyl azides provides a convenient route to N-alkyl anilines (see scheme; DG=directing group). Alkyl azides with a wide range of functional groups reacted readily with various substrates, including benzamides, aromatic ketones, and flavones. Copyright

A simple and efficient bromoformyloxylation and bromoacetoxylation reaction using TsNBr2

Bromoformyloxylation and bromoacetoxylation of olefins proceed smoothly and instantaneously in the presence of N,N-dibromo-p-toluene sulfonamide without any catalyst. The one step reactions can be carried out with all kinds of olefins in high yield and hi

Addition of halide to π-bond directly from aqueous NaX solution: A general strategy for installation of two different functional groups

Activation of π-bond with organic Lewis acid and cationic surfactant mediated direct transfer of halides to alkyne and alkene are demonstrated to afford α,α-dihaloketones and other valuable synthons with outstanding selectivities.

Palladium-catalyzed reaction of olefins with PhI(OAc)TBAB system: An efficient and highly selective bisfunctionalization strategy

The palladium-catalyzed reaction of olefins with PhI(OAc)TBAB system provides a novel, efficient, and highly selective bisfunctionalization strategy to introduce bromo and oxygen groups simultaneously. The substituents on the C=C bond control the regiosel