187409-10-5

Upstream product

• 2039-85-2 3-Chlorostyrene 
• 620-16-6 3-chloroethylbenzene 
• 36229-42-2 (3-chlorophenyl)magnesium bromide 
• 65130-47-4 3-chloro-α-bromoethylbenzene 
• 32503-27-8 tetra(n-butyl)ammonium hydrogensulfate 
• 672-65-1 (1-chloroethyl)benzene 
• 587-04-2 m-Chlorobenzaldehyde 
• 120121-01-9 1-(m-Chlorophenyl)ethanol 

Downstream Products

• 2039-85-2 3-Chlorostyrene 
• 117538-45-1 2-bromo-1-(3-chlorophenyl)ethanol 
• 89619-10-3 1-(1-bromovinyl)-4-chlorobenzene 
• 187409-14-9 1-(1-bromovinyl)-3-chlorobenzene 
• 61001-11-4 2-(3-chlorophenyl)imidazo[2,1-a]isoquinoline 
• 419557-36-1 2-(3-chlorophenyl)-7-methylimidazo[1,2-a]pyridine 
• 217939-59-8 Propionic acid (S)-2-bromo-1-(3-chloro-phenyl)-ethyl ester 
• 194721-60-3 (S)-2-bromo-1-(3-chlorophenyl)ethyl acetate 
• 174699-77-5 (R)?2?bromo?1?(3′?chlorophenyl)ethanol 
• 115648-90-3 (S)-3-chlorostyrene oxide 
• 20697-04-5 (R)-meta-chlorostyrene oxide 
• 133220-30-1 2-[2-(3-chloro-phenyl)-oxiranylmethyl]-2-ethyl-1H-indene-1,3(2H)-dione 
• 133220-63-0 2-<2-(3-chlorophenyl)prop-2-enyl>-2-ethylindane-1,3-dione 
• 133220-70-9 3-chloro-α-(chloromethyl)-styrene 

Relevant academic research and scientific papers

A practical synthesis of 3-chloro-α-bromostyrene starting from 3- chloroethylbenzene

3-Chloro-α,β-dibromoethylbenzene was prepared via I2 catalyzed bromination of 3-chloro-α-bromoethylbenzene. It was dehydrobrominated with aqueous NaOH in the presence of n-Bu4N+HSO4- to give 3-chloro-

The intramolecular reaction of acetophenoneN-tosylhydrazone and vinyl: Br?nsted acid-promoted cationic cyclization toward polysubstituted indenes

In the presence of TsNHNH2, a Br?nsted acid-promoted intramolecular cyclization ofo-(1-arylvinyl) acetophenone derivatives was developed, leading to polysubstituted indenes with complexity and diversity in moderate to excellent yields. In sharp contrast with either the radical or carbene involved cyclization of aldehydicN-tosylhydrazone with vinyl, a cationic cyclization pathway was involved, whereN-tosylhydrazone served as an electrophile and alkylation reagent during this transformation.

Visible-Light-Induced Regioselective C(sp3)-H Acyloxylation of Aryl-2 H-azirines with (Diacetoxy)iodobenzene

A visible-light-promoted regioselective coupling of C(sp3)-H of aryl-2H-azirine and (diacetoxy)iodobenzene has been reported. Rose Bengal as an organophotoredox catalyst has been used in this reaction. The reaction proceeds under aerobic condition at room temperature. A variety of aryl-2H-azirines gives the corresponding acyloxylated azirines under this reaction conditions. The reaction goes through a radical pathway. The protocol is also applicable on gram-scale synthesis.

Mild and Efficient Vicinal Dibromination of Olefins Mediated by Aqueous Ammonium Fluoride

A mild and efficient vicinal dibromination of olefins has been developed by using saturated aqueous ammonium fluoride solution as the promoter. Inexpensive and commercially available N -bromosuccinimide (NBS) was used as the brominating reagent. The corresponding vicinal dibromoalkanes could be obtained in good to excellent yields.

Visible-Light Photoredox Catalyzed Three-Component Cyclization of 2H-Azirines, Alkynyl Bromides, and Molecular Oxygen to Oxazole Skeleton

A novel three-component cyclization of 2H-azirines, alkynyl bromides, and molecular oxygen under visible-light photoredox catalysis at room temperature has been developed, which provides a direct approach to a wide range of substituted oxazoles in moderate to good yields.

I2-catalyzed synthesis of substituted imidazoles from vinyl azides and benzylamines

A novel and efficient I2-catalyzed oxidative tandem cyclization of simple vinyl azides and benzylamines has been developed for the synthesis of substituted imidazoles. In this reaction, various substituted groups on vinyl azides and benzylamines proceed smoothly and the desired imidazoles are obtained in moderate to good yields.

3-substituted-α, β-dibromoethylbenzene and process for preparing the same

A novel 3-substituted α,β-dibromoethylbenzene of formula (I): STR1 wherein X represents a halogen atom or a trihalomethyl group, which is useful as an intermediate for pharmaceuticals or agricultural chemicals, is prepared by a simple and high yield proce

Use of kinetic isotope effects in mechanism studies. Isotope effects and element effects associated with Hydron-Transfer steps during alkoxide-promoted dehydrohalogenations

The Arrhenius behavior of the primary kinetic isotope effect, (k(H)/k(D))(Obs) and (k(H)/k(T))(Obs), associated with the methanolic sodium methoxide-promoted dehydrohalogenations of m-ClC6H4C(i)HClCH2Cl (I), m-CF3C6H4C(i)-HClCH2Cl (II) and p-CF3C6H4C(i)HClCH2F (III) has been used to calculate the internal-return parameters, a = k(-1)/K(Elim)(X), in a two-step mechanism featuring a hydrogen-bonded carbanion. This carbanion partitions between returning the hydron to carbon, k(-1), and the loss of halide, K(Elm)(X). Isotope effects at 25°C for I, (k(H)/k(D))(Obs) = 3.40 and (k(H)/ k(T))(Obs) = 6.20, and II, (k(H)/k(D))(Obs) = 3.49 and (k(H)/k(T))(Obs) = 6.55, result in similar values for a: a(H) = 0.59, a(D) = 0.13-0.14 and a(T) = 0.07. Smaller values of (k(H)/k(D))(Obs) = 2.19 and (k(H)/k(T))(Obs) = 3.56 for III are due to more internal return [a(H) = 1.9, a(D) = 0.50, and a(T) = 0.28] associated with the dehydrofluorination reaction. Calculation of k1 ( k(Obs) [a + 1]) results in similar isotope effects for hydron transfer in these reactions: k1(H)/k1(D) = 4.74 and k1(H)/K1(T) = 9.20; II, k1(H)/k1(D) = 4.91 and k1(H)/k1(T) = 9.75; III, k1(H)/k1(D) = 4.75 and k1(H)/k1(T) = 9.17. Reactions of m-ClC6H4C(i)HBrCH2Br and m-ClC6H4C(i)HClCH2Br have very small amounts of internal return, a(H) = 0.05 and a(D) = 0.01, and (k(H)/k(D))(Obs) = 4.95 results in k1(H)/k1(D) = 5.11 The measured isotope effects are therefore due to differences in the amount of internal return and not in the symmetry of transition state structures for the hydron transfer, and the element effect, (k(HBr)/ k(HCl)) = 29, for m-ClC6H4CHClCH2X is mainly due to the hydron-transfer step, k1(HBr)/k1(HCl) = 19, and not the breaking of the C-X bend. The kinetic solvent isotope effects, k(MeOD)/k(MeOH) ~ 2.5, are consistent with three methanols of solvation lost prior to the hydron-transfer step. The energetics associated with desolvation of methoxide ion are part of the measured reaction energetics of these systems.