450412-27-8

Usage

Uses

Used in Organic Synthesis:
Ethyl 5-bromo-2-iodobenzoate is used as a building block in organic synthesis for the construction of more complex organic molecules. The presence of bromine and iodine atoms allows for further chemical reactions and modifications, making it a versatile compound in the synthesis of various organic compounds.
Used in Pharmaceutical Industry:
Ethyl 5-bromo-2-iodobenzoate is used as a precursor in the preparation of pharmaceuticals. Its unique structure and functional groups make it a valuable intermediate in the synthesis of various drug molecules. The bromine and iodine atoms can be further modified or replaced to create new pharmaceutical compounds with specific therapeutic properties.
Used in Agrochemical Industry:
Ethyl 5-bromo-2-iodobenzoate is also used as a precursor in the preparation of agrochemicals. Its chemical properties and reactivity make it suitable for the synthesis of various agrochemicals, such as pesticides and herbicides. The bromine and iodine atoms can be utilized to create new agrochemical compounds with improved efficacy and selectivity.
Safety Precautions:
It is important to handle ethyl 5-bromo-2-iodobenzoate with caution, as both bromine and iodine are known to be toxic and can cause irritation to the skin, eyes, and respiratory system if handled improperly. Proper safety measures, such as wearing protective clothing, gloves, and eye protection, should be taken to minimize the risk of exposure and potential health hazards.

Upstream product

• 1829-28-3 ethyl 2-iodobenzoate 
• 64-17-5 ethanol 
• 21740-00-1 5-bromo-2-iodo-benzoic acid 
• 24398-88-7 ethyl 3-bromobenzoate 

Downstream Products

• 689291-89-2 5-bromo-2-iodobenzaldehyde 
• 1026089-66-6 3-(4-bromo-2-ethoxycarbonyl-phenyl)-pyrrole-1-carboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

Critical Ligand and Salt Effects in Organomagnesiate-Promoted 3,3-Disubstituted Phthalides Synthesis from 2-Iodobenzoate Derivatives

Phthalides, also called isobenzofuranones, are widespread in many biologically active compounds and natural products. To date, most of their synthetic routes are non-convergent. Herein we report a convergent route using a metal halogen exchange (MHE) strategy. Indeed MHE of easily available 2-iodobenzoate derivatives, using the bimetallic organomagnesiate complex (rac)-(BIPHEN)BuMgLi, where (rac)-BIPHEN is (rac)-5,5′,6,6′-tetramethyl-3,3′-di-t-butyl-1,1′-biphenyl-2,2′-diol, followed by addition of a ketone which lead to an intramolecular cyclisation, and the formation of a series of diverse 3,3-disubstituted isobenzofuranones in good yield. Among the several MHE agents investigated, (rac)-(BIPHEN)BuMgLi was the only one to make such a process possible with full tolerance of various reactive functional substituents useful for subsequent transformations. The synthetic pathway to access the magnesiate has been found to play a prominent role in its reactivity. Therefore, the bimetallic magnesiate complex has been characterized by solution-state 1H, 7Li and 1H DOSY NMR experiments.

One-Pot C-H Arylation/Lactamization Cascade Reaction of Free Benzylamines

An efficient method has been developed for the synthesis of seven-membered biaryl lactams involving Pd-catalyzed, native amine-directed, ortho-arylation of benzylamines followed by in situ lactamization. This cascade sequence is enabled by the use of 2-iodobenzoates, which facilitates C-H arylation from the free amine under conditions that typically require an improved directing group approach. This reaction is characterized by a broad substrate scope with good functional group tolerance. The need for an ester versus carboxylic acid-functionalized coupling partner is also explored, as is the potential for synthesizing eight-membered biaryl lactams. Various applications are also investigated, including access to the aza-brassinolide core.

Generation and suppression of 3-/4-functionalized benzynes using zinc ate base (TMP-Zn-ate): New approaches to multisubstituted benzenes

We present full details of our new methods for preparing functionalized benzynes with lithium di-alkyl(2,2,6,6-tetramethylpiperidino)zincate (R 2Zn(TMP)Li) through deprotonative zincation as a key reaction. In this system, by choosing appropriate ligands for the zincate, either regioselective zincation of functionalized haloaromatics or the generation of substituted benzynes can be controlled in good yields with excellent chemoselectivity, using the same substrate. Zincation with tBu 2Zn(TMP)Li followed by electrophilic trapping or zincation with Me2Zn(TMP)Li followed by nucleophilic or diene trapping is shown to be a powerful tool for the chemoselective preparation of 1,2,3-/1,2,4- trisubstituted benzene derivatives. These methods offer far greater generality than previous methods for the synthesis of multifunctionalized benzenes. Computational/theoretical studies of the reaction mechanism of this unique benzyne formation indicated that preferential coordination of the dialkylzinc moiety of zincate to halogen is the reason for the reduced activation energy of the elimination, that is, for the formation of the benzyne. The role of the ligands on Zn in accelerating/decelerating the elimination is also discussed.

ARYLSULFONYL PYRROLIDINES AS 5-HT6 INHIBITORS

This invention relates to substituted pyrrolidine compounds of the formula I wherein m, n, Ar, R1 and R2 are as defined herein. Methods of making the compounds and using the compounds are disclosed.

Generation of functionalized asymmetric benzynes with TMP-zincates. Effects of ligands on selectivity and reactivity of zincates

We have developed new methods for preparing functionalized benzynes through deprotonative zincation as a key reaction using R2Zn(TMP)Li, and we also describes dramatic ligand effects on the benzyne formation. Deprotonative zincation of various meta-substituted bromobenzenes with Me2Zn(TMP)Li proved effective for the one-pot generation of various 3-functionalized benzynes, particularly those electrophilic substituents such as ester, amide, and cyano. On the other hand, zincation with tBu2Zn(TMP)Li, followed by electrophilic trapping (with I2) proved a powerful tool for the preparation of 1,2,3-trisubstituted aromatic compounds.8 The resultant 1,2,3-trisubstituted benzenes are available as precursors for generation of 3-substituted benzynes by halogen-zinc exchange reactions with Me3ZnLi. These methods offer far greater generality than previous methods for the synthesis of functionalized asymmetric benzynes, and should be of value in new syntheses of various natural products and functional materials. In addition, these results underline the utility of spectator ligands on the central metal of ate complexes as a tunable functionality in the development of new ate complex-promoted reactions. Copyright