22543-77-7

Upstream product

• 83-38-5 2,6-dichlorobenzaldehyde 
• 100-52-7 benzaldehyde 
• 541-73-1 1,3-Dichlorobenzene 
• 1623-99-0 phenyl sodium 
• 19393-92-1 1-bromo-2,6-dichlorobenzene 

Downstream Products

• 1218781-14-6 C₁₃H₉Cl₃ 

Relevant academic research and scientific papers

Sodiation of Arenes and Heteroarenes in Continuous Flow

The first sodiations of (hetero)arenes in continuous flow using NaDA (sodium diisopropylamide) in Me2EtN are reported. This flow procedure enables sodiation of functionalized arenes and heteroarenes that decompose under batch-sodiation conditions. The resulting sodiated (hetero)arenes react instantly with various electrophiles, such as ketones, aldehydes, isocyanates, alkyl bromides, and disulfides, affording polyfunctionalized (hetero)arenes in high yields. Scale-up is possible without further optimization.

Directed magnesiation of polyhaloaromatics using the tetramethylpiperidylmagnesium reagents TMP2Mg×2 LiCl and TMPMgCl×LiCl

A convenient and efficient functionalization of polyhaloaromatics via regioselective magnesiation has been developed. Starting from simple, inexpensive but structurally challenging arenes, metallation by magnesium amide bases was achieved under mild conditions. The desired Grignard reagents were stable towards aryne formation, were obtained in good yields within short reaction times and could be reacted with a variety of typical electrophiles, providing attractive, functionalized building blocks in good to excellent yields. As an application we have prepared the antimicrobial natural product 2,6-dichloro-3-phenethylphenol isolated from the New Zealand liverwort Riccardia marginata. This synthesis involves a mixed bimetallic compound prepared via metallation of a phenylboronic acid pinacol ester derivative and subsequent selective cross-coupling. Copyright

Method of preparing organomagnesium compounds

The present invention is directed to a reagent for use in the preparation of organomagnesium compounds as well as to a method of preparing such organomagnesium compounds. The present invention furthermore provides a method of preparing functionalized or unfunctionalized organic compounds as well as the use of the reagents of the present invention in the preparation of organometallic compounds and their reaction with electrophiles. Finally, the present invention is directed to the use of lithium salts - LiY in the preparation of organometallic compounds and their reactions with electrophiles and to an organometallic compound which is obtainable by the disclosed method.

A LiCl-mediated Br/Mg exchange reaction for the preparation of functionalized aryl- and heteroarylmagnesium compounds from organic bromides

A wide range of aryl and heteroaryl bromides, which are usually sluggish in exchange reactions, are readily converted into the corresponding Grignard reagents by means of a Br/Mg exchange reaction triggered by iPrMgCl·LiCl (see scheme). These Grignard intermediates react with electrophiles in good yields.

Process for producing benzhydrols

There is disclosed a process for producing benzhydrls by reacting an arylmetal compound with an aromatic aldehyde. According to this process, benzhydrols useful as raw materials for medicines and photopolymerization initiators can be produced in a high yield and industrially advantageously.

Synthesis, Stability, and Reactions of 2,6-Dichlorophenyllithium

A convenient, general, and regioselective synthesis of 2,6-dichloroaromatic compounds from m-dichlorobenzene is described.The stability of 2,6-dichlorophenyllithium is examined.