187409-14-9

Upstream product

• 187409-10-5 3-chloro-α,β-dibromoethylbenzene 
• 620-16-6 3-chloroethylbenzene 
• 99-02-5 3'-Chloroacetophenone 
• 766-83-6 m-chlorophenylacetylene 
• 74-95-3 1,1-dibromomethane 
• 2039-85-2 3-Chlorostyrene 

Downstream Products

• 157563-52-5 2-(3-chlorophenyl)prop-2-en-1-ol 
• 41011-01-2 2-bromo-1-(3-chloro-phenyl)-ethanone 
• 147374-00-3 ethyl 4-(3-chlorophenyl)-4-oxobutanoate 
• 133220-30-1 2-[2-(3-chloro-phenyl)-oxiranylmethyl]-2-ethyl-1H-indene-1,3(2H)-dione 

Relevant academic research and scientific papers

Catalytic Asymmetric Halogenation/Semipinacol Rearrangement of 3-Hydroxyl-3-vinyl Oxindoles: A Stereodivergent Kinetic Resolution Process

A highly enantioselective halogenation/semipinacol rearrangement of isatin-derived allylic alcohols has been developed with a chiral N,N′-dioxide/ScIII complex as catalyst. This strategy involved a pivotal stereodivergent kinetic resolution process and provided a facile and efficient entry to optically active halo-substituted quinolone derivatives and quinoline alkaloids with a quaternary stereocenter simultaneously under mild reaction conditions. Based on the control experiments together with kinetic studies and DFT calculations, a possible catalytic cycle was proposed to illustrate the reaction process and enantiocontrol.

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.

Synthesis of Unsymmetrical 1,4-Dicarbonyl Compounds by Photocatalytic Oxidative Radical Additions

Herein we report a photocatalytic oxidative radical addition reaction for the synthesis of unsymmetrical 1,4-dicarbonyl compounds. This reaction utilizes a desulfurization process to generate electrophilic radicals, which add to α-halogenated alkenes and undergo further oxidation to deliver 1,4-dicarbonyl compounds. This mild and highly efficient method provides a valuable alternative to known strategies.

Electrochemical Semipinacol Rearrangements of Allylic Alcohols: Construction of All-Carbon Quaternary Stereocenters

The first examples of electrochemical trifluoromethylation and sulfonylation/semipinacol rearrangements of allylic alcohols were developed using cheap and stable RSO2Na (R = CF3, Ph) as reagents. Various β-trifluoromethyl and sulfonated ketones were obtained in moderate to excellent yields. This strategy provides a facile, direct, and complementary approach to construct all-carbon quaternary stereocenters. In addition, the reaction has the advantages of being chemical oxidant-free and metal-free and has safe and mild reaction conditions.

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-

A practical synthesis of indanofan via one-pot bromination of 3- chloroethylbenzene

A practical synthesis of Indanofan (1), a potent herbicide discovered by Mitsubishi Chemical Co. Ltd., was achieved starting from commercially available 3-chloroethylbenzene (2). 3-Chloro-α-bromostyrene (3), which was converted to 1-chloro-2-(3-chlorophenyl)prop-2-ene (5) in 2 steps, was synthesized via one-pot bromination of 2. 2-Ethylindane-1,3-dione (6) was synthesized from ethyl butyrate and ethyl phthalate (11) using NaOEt. The coupling reaction of 5 with 6 followed by oxidation with AcOOH afforded 1 in a high overall yield.