6314-52-9

Upstream product

• 555-31-7 aluminum isopropoxide 
• 536-38-9 4-chlorobenzoylmethyl bromide 
• 1073-67-2 4-vinylbenzyl chloride 
• 2788-86-5 4-Chlorostyrene oxide 
• 3391-10-4 1-(p-chlorophenyl)ethyl alcohol 
• 23135-16-2 1,2-dibromo-1-(4-chlorophenyl)ethane 

Downstream Products

• 57265-96-0 1-(p-chloro-β-hydroxyphenethyl)-3-[2,4-dichloro-β-(2,6-dichlorobenzyloxy)phenethyl]imidazolium bromide 
• 2788-86-5 4-Chlorostyrene oxide 
• 536-38-9 4-chlorobenzoylmethyl bromide 
• 66482-30-2 (Z)-1-bromo-2-(4-chlorophenyl)ethylene 
• 66482-29-9 1-[(E)-2-bromoethenyl]-4-chlorobenzene 
• 179065-35-1 (S)?2?bromo?1?(4′?chlorophenyl)ethanol 
• 182621-75-6 (R)?2?bromo?1?(4′?chlorophenyl)ethanol 
• 2788-86-5 (2S)-2-(4-chlorophenyl)oxirane 

Relevant academic research and scientific papers

Alkene, Bromide, and ROH – How To Achieve Selectivity? Electrochemical Synthesis of Bromohydrins and Their Ethers

Bromohydrins and their ethers were electrochemically synthesized via hydroxy- and alkoxybromination of alkenes using potassium bromide and water or alcohols. High selectivity of bromohydrins formation was achieved only with the use of DMSO as the solvent and an acid as the additive. The proposed combination of starting reagents, additives, and solvents allowed to form bromohydrins or their ethers selectively despite the variety of side-products (epoxides, dibromides, diols). Bromohydrins were obtained in high yields, up to 96%, with a broad substrate scope in an undivided electrochemical cell equipped with glassy carbon and platinum electrodes at high current density. (Figure presented.).

Electrochemical bromofunctionalization of alkenes in a flow reactor

The bromination of organic molecules has been extensively studied to date, yet there is still a demand for safe and sustainable methodologies. Hazardous reagents, selectivity, low atom economy and waste production are the most persisting problems of brominating reagents. The electrochemical oxidation of bromide to bromine is a viable strategy to reduce waste by avoiding chemical oxidants. Furthermore, thein situgeneration of reactive intermediates minimizes the risk of hazardous reagents. In this work, we investigate the electrochemical generation of bromine from hydrobromic acid in a flow electrochemical reactor. Various alkenes could be converted to their corresponding dibromides, bromohydrines, bromohydrin ethers and cyclized products in good to excellent yields.

Cascade bio-hydroxylation and dehalogenation for one-pot enantioselective synthesis of optically active β-halohydrins from halohydrocarbons

A stereoselective hydroxylation and enantioselective dehalogenation cascade reaction was developed for the synthesis of optically active β-haloalcohols from halohydrocarbons. This cascade system employed P450 and halohydrin dehalogenase as two compatible biocatalysts, allowing a straightforward, greener and efficient access to β-halohydrins with excellent enantioselectivities (98-99%).

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.

I2O5-mediated bromohydroxylation and dibromination of olefins using KBr in water

An efficient and green bromohydroxylation and dibromination of various olefins mediated by I2O5 has been developed in this work. A series of olefins gave the corresponding α-bromo-alcohols and dibromides as the major products using KBr as the brominating reagent in aqueous medium at room temperature. The diastereo- and regio-selectivities are extremely high.

Synthesis of bromohydrins using NBS in presence of iodine as catalyst

Iodine has been found to catalyze bromohydrin formation reaction using NBS as a brominating agent. The procedure is efficient and produces high yield of the product at 0°C within a short time. Cinnamic esters can easily be transformed to corresponding bromohydrins in high yield.

Synthesis of Di-, Tri-, and tetrasubstituted oxetanes by rhodium-catalyzed O-H insertion and C-C bond-forming cyclization

Oxetanes offer exciting potential as structural motifs and intermediates in drug discovery and materials science. Here an efficient strategy for the synthesis of oxetane rings incorporating pendant functional groups is described. A wide variety of oxetane 2,2-dicarboxylates were accessed in high yields, including functionalized 3-/4-aryl-and alkyl-substituted oxetanes and fused oxetane bicycles. Enantioenriched alcohols provided enantioenriched oxetanes with complete retention of configuration. The oxetane products were further derivatized, while the ring was maintained intact, thus highlighting their potential as building blocks for medicinal chemistry.

Mechanism-guided design of flow systems for multicomponent reactions: Conversion of CO2 and olefins to cyclic carbonates

A mechanism-guided design of a multi-step flow system enabled an efficient general process for the synthesis of cyclic carbonates from alkenes and CO 2. The flow system proved to be an ideal platform for multicomponent reactions because it was straightforward to introduce reagents at specific stages without their interacting with each other or with reaction intermediates prone to destruction by them. This system exhibited superior reactivity, increased yield, and broader substrate scope relative to conventional batch conditions and suppressed the formation of undesired byproducts, such as, epoxides and 1,2-dibromoalkanes. The Royal Society of Chemistry 2014.

Unconserved substrate-binding sites direct the stereoselectivity of medium-chain alcohol dehydrogenase

Structure-guided design of substrate-binding pocket inversed the stereoselectivity of an NADH-dependent medium-chain alcohol dehydrogenase (MDR) from Prelog to anti-Prelog. The pocket-forming amino acids, especially the unconserved residues as hotspots, play critical roles in directing MDRs' stereoselectivity. This journal is the Partner Organisations 2014.

BNBTS More than brominating agent: Green and one-pot route for the C-N bond formation in water from alkenes

In this paper, in addition to introducing efficient method for bromohydrin and bromoether preparation, simple, green and efficient method to C-N bond formation from alkene and N,N'-Dibromo-N,N'-1,2-ethanediyl- bis(ptoluenesulfonamide) [BNBTS] in water was investigated. The reaction between alkenes, β-cyclodexterin, and BNBTS took place in water afterward, by making media basic; it will give the corresponding valuable building blocks in good yields (45-79%).