35115-84-5

Upstream product

• 67-56-1 methanol 
• 35115-76-5 2,3-dichloro-3-phenyl-propionic acid 
• 103-26-4 methyl cinnamate 
• 103-26-4 Methyl cinnamate 
• 68-12-2 N,N-dimethyl-formamide 
• 694-59-7 pyridine N-oxide 
• 19713-73-6 methyl (2Z)-3-phenylprop-2-enoate 

Downstream Products

• 705-54-4 (Z)-α-chlorocinnamic acid 
• 14737-94-1 methyl 2-chloro-3-phenylprop-2(Z)-enoate 
• 4519-51-1 α-chlorocinnamic acid methyl ester 
• 4519-51-1 (E)-2-chloro-3-phenylacrylic acid methyl ester 

Relevant academic research and scientific papers

Merging shuttle reactions and paired electrolysis for reversible vicinal dihalogenations

Vicinal dibromides and dichlorides are important commodity chemicals and indispensable synthetic intermediates in modern chemistry that are traditionally synthesized using hazardous elemental chlorine and bromine. Meanwhile, the environmental persistence of halogenated pollutants necessitates improved approaches to accelerate their remediation. Here, we introduce an electrochemically assisted shuttle (e-shuttle) paradigm for the facile and scalable interconversion of alkenes and vicinal dihalides, a class of reactions that can be used both to synthesize useful dihalogenated molecules from simple alkenes and to recycle waste material through retro-dihalogenation. The reaction is demonstrated using 1,2-dibromoethane, as well as 1,1,1,2-tetrachloroethane or 1,2-dichloroethane, to dibrominate or dichlorinate, respectively, a wide range of alkenes in a simple setup with inexpensive graphite electrodes. Conversely, the hexachlorinated persistent pollutant lindane could be fully dechlorinated to benzene in soil samples using simple alkene acceptors.

A simple and highly diasteroselective approach for the vicinal dichlorination of functional olefins

Organocatalytic stereospecific vicinal dicholorination of a wide variety of functionalized olefins such as ketoesters, esters, ketones, carvone, cholesterol and ethyl sorbate (27 examples) was achieved using inexpensive sulfuryl chloride as well as a simple phosphine catalyst under mild reaction conditions. The products were obtained with good to excellent yields and diastereoselectivities (up to 96% yield and >25 : 1 dr).

Vicinal dichlorination of olefins using NH4Cl and oxone

A mild and efficient protocol for the preparation of 1,2-dichloroalkane derivatives from olefins using NH4Cl and Oxone at room temperature is described. A variety of terminal, internal, and cyclic alkenes reacted smoothly to give the corresponding dichlorinated products in good to excellent yields. Moreover, 1,2-disubstituted symmetrical and unsymmetrical olefins dichlorinated with moderate to excellent diastereoselectivity. This method precludes the use of acidic additives and transition metals in the synthesis of vicinal dichlorides.

Simple and practical halogenation of arenes, alkenes and alkynes with hydrohalic acid/H2O2 or TBHP)

A simple protocol for the halogenation of arenes utilizing a combination of aqueous hydrogen peroxide (34 %) or tert-butylhydroperoxide (70 %) and hydrohalic acid is presented. A similar procure of oxyhalogenation involving the in situ generation of positive halogen reagents is applied for the preparation of vicinal trans-dibromoalkanes and dichloroalkanes from alkenes. The reaction of alkenes with a combination of hydrochloric acid and hydrobromic acid with hydrogen peroxide gave a mixture of 1-bromo 2-chloro alkanes and 1,2-dibromoalkanes: Oxidative bromination of alkynes is also reported under similar conditions.

Synthesis of chloroalkoxypyridinium salts by conjugate chlorination of unsaturated compounds in the presence of pyridine N-oxides

Conjugate chlorination of terminal alkenes in the presence of pyridine N-oxides yields mixtures of regioisomeric chloroalkoxypyridinium chlorides. The same reaction with internal arylalkenes is regioselective, but the resulting quaternary salt is a mixture of erythro and threo stereoisomers.

The reactions of α,β-unsaturated esters by HCL/DMF/oxone system

The reactions of α,β-unsaturated esters by HCl/DMF/Oxone system afforded four different chlorinated products 2-5 in variable yields.

Reaction of Benzeneseleninyl Chloride with Olefins in the Presence of a Lewis Acid. A Novel One Step Vinylic Chlorination

In the presence of aluminum chloride benzeneseleninyl chloride was found to be an exellent vinylic chlorinating reagent of olefins under mild conditions.However, such olefins as styrene, trans-stilbene, and trans-1-phenylpropene afforded dichloro adducts under similar conditions.A plausible reaction mechanism involving positive chlorine intermediate is proposed.

PREPARATION AND Z-E ISOMERIZATION OF SUBSTITUTED NITROSTYRENES

This study concerns the synthesis of β-substituted β-nitrostyrenes by two procedures: addition of nitryl halogenides to double bonds, connected with the elimination of hydrogen halide, and condensation of aldehydes with substituted nitromethanes, and it c

CHLORINATION OF ALKENES BY MANGANESE(III) CHLORIDE SPECIES

Several manganese(III) chloride species have been prepared in situ and used as effective chlorinating agents of alkenes.

Synthesis of Novel 1,3-Dithiolan-2-one Derivatives

Novel 1,3-dithiolan-2-one derivatives were prepared starting from α,β- or β,γ-dichlorinated carboxylic esters and potassium O-ethyl dithiocarbonate.The scope and the mechanism of this reaction were investigated.The biological uses of the compounds obtained here were examined.