333309-74-3

Upstream product

• 704-96-1 trans-2-chlorocinnamic acid 
• 2039-87-4 2-chlorostyrene 
• 3752-25-8 o-chlorocinnamic acid 
• 1355094-04-0 (E)-2-(2-chlorostyryl)-4,4,5,5-tetramethyl-1,3-dioxa-2-borolane 
• 72702-57-9 2-Bromo-1-(2-chlorophenyl)ethan-1-ol 
• 401514-40-7 1-chloro-2-(2,2-dibromovinyl)benzene 
• 1034-49-7 (bromomethyl)triphenyl phosphonium bromide 
• 89-98-5 2-chloro-benzaldehyde 
• 24654-07-7 (2RS,3SR)-2,3-dibromo-3-(2-chlorophenyl)propanoic acid 

Downstream Products

• 1085710-25-3 (E)-1-chloro-2-(2-iodovinyl)benzene 
• 1467023-74-0 (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-{[(E)-2-chlorostyryl]thio}tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 1201221-08-0 C₁₇H₁₃ClO 
• 51220-00-9 (E)-3-(2-chlorophenyl)-2-propenenitrile 

Relevant academic research and scientific papers

Metal-Mediated Debromination of gem-Dibromoalkenes under Mild Conditions

We describe the facile and efficient metal-promoted reduction of C-Br bonds of gem-dibromides. When the reaction is mediated by indium, the corresponding vinyl bromides are obtained in good yields and high E-stereoselectivities. Alternatively, when the reduction is mediated by samarium diiodide, vinyl bromides are obtained in moderate yields and good Z-selectivities.

Cyclic Diaryl λ3-Bromanes: A Rapid Access to Molecular Complexity via Cycloaddition Reactions

Biaryls have widespread applications in organic synthesis. However, sequentially polysubstituted biaryls are underdeveloped due to their challenging preparation. Herein, we report the synthesis of dissymetric 2,3,2′,3′,4-substituted biaryls via pericyclic reactions of cyclic diaryl λ3-bromanes. The functional groups tolerance and atom economy allow access to molecular complexity in a single reaction step. Continuous flow protocol has been designed for the scale-up of the reaction, while postfunctionalizations have been developed taking advantage of the residual Br-atom.

Method for synthesizing beta-bromostyrene through metal-free catalysis

The invention discloses a method for synthesizing beta-bromostyrene through metal-free catalysis, and belongs to the technical field of organic chemistry. Substituted styrene 1 is used as a raw material and is reacted in the presence of a bromination reagent, sodium persulfate and dichloroethane, and the beta-bromostyrene compound 2 can be obtained in one step. The method is capable of solving thetechnical problem that in the traditional synthesis method, conversion into alkenyl boron, alkenyl silicon and other intermediates under the catalysis of noble metals and then further halogenation are needed; the defects of expensive reaction reagent, high catalytic cost, complex operation, incapability of large-scale preparation and the like in the traditional preparation method are avoided; byadopting the method, a series of beta-bromostyrene compounds can be obtained, and the method has a potential application prospect.

Facile Synthesis of β-Bromostyrenes by Direct Bromination of Styrenes with N -Bromosuccinimide and Sodium Persulfate

A new, direct, efficient, and transition-metal-free method is reported for the synthesis of β-bromostyrenes from styrenes by using N -bromosuccinimide as the brominating reagent and sodium persulfate (Na 2S 2O 8) as the oxidant. This convenient and concise reaction is practical, operationally simple, and can be adapted for large-scale syntheses.

Decarboxylative bromination of α,β-unsaturated carboxylic acids via an anodic oxidation

A novel bromination of α,β-unsaturated carboxylic acids was developed via a decarboxylation by virtue of a direct anodic electro-oxidation. In this method, ammonium bromide was employed as a bromine source and the reaction features transition-metal-free, short time, and no additional supporting electrolyte.

Stereoselective Synthesis of Vinyl Iodides through Copper(I)-Catalyzed Finkelstein-Type Halide-Exchange Reaction

An efficient method for the stereoselective synthesis of vinyl iodides is described. The reactions of vinyl bromides with potassium iodide proceed smoothly in the presence of a copper catalyst under mild reaction conditions to produce the corresponding vinyl iodides stereospecifically and in satisfactory to excellent yields.

A stereoselective synthesis of (E)- or (Z)-β-arylvinyl halides via a borylative coupling/halodeborylation protocol

A new stereoselective method for the synthesis of (E)-β-arylvinyl iodides and (E)- or (Z)-β-arylvinyl bromides from styrenes and vinyl boronates on the basis of a one-pot procedure via borylative coupling/halodeborylation is reported. Depending on the halogenating agent as well as the mode of the halodeborylation reaction, (E) or (Z) isomers are selectively formed.

Ohmic Heating and Ionic Liquids in Combination for the Indium-Promoted Synthesis of 1-Halo Alkenyl Compounds: Applications to Pd-Catalysed Cross-Coupling Reactions

We have explored the combination of ohmic heating (ΩH) with ionic liquids for indium-promoted reactions and report herein the indium-promoted dehalogenation of gem-dibromo alkenes and the indium-mediated reductive elimination of chlorohydrins for the synthesis of 1-halo alkenyl derivatives. Heck, Stille, Suzuki, Kumada and Sonogashira couplings of the resulting 1-halo-1-alkenes with appropriate reagents were carried out to give alkenes, dienes and enynes. We report herein the combination of ohmic heating (ΩH) with ionic liquids for the indium-promoted dehalogenation of gem-dibromo alkenes and the indium-mediated reductive elimination of chlorohydrins. The 1-halo alkenyl derivatives synthesized were then submitted to a series of cross-coupling reactions to give conjugated alkenes, dienes and enynes.

Tellurium-promoted stereoselective hydrodebromination of 1,1-dibromoalkenes: Synthesis of (: E)-bromoalkenes

We describe herein an efficient and simple method for the stereoselective hydrodebromination of 1,1-dibromoalkenes by using a catalytic amount of the nucleophilic species of tellurium, generated in situ by the reaction of elemental tellurium with NaBH4. By this methodology, (E)-bromoalkenes were obtained in moderate to excellent yields under mild reaction conditions, without the use of transition metals or base. Furthermore, a high stereoselectivity for the (E)-isomer was observed when 1,1-dibromoarylalkenes were used, thus indicating a promising alternative for future applications in organic synthesis.

H-β-zeolite catalyzed synthesis of β-bromostyrenes from styrene bromohydrins

Synthesis of β-bromostyrenes from styrene bromohydrins using H-β-zeolite as catalyst under moderate conditions is reported. The catalyst could be regenerated and reused up to three consecutive cycles.