54008-77-4

Usage

Uses

Used in Pharmaceutical Synthesis:
2-BROMO-1-BENZOFURAN is used as a building block for the synthesis of various pharmaceuticals, leveraging its unique structure and reactivity to form essential carbon-carbon and carbon-heteroatom bonds in the development of new drugs.
Used in Organic Chemistry:
In the field of organic chemistry, 2-BROMO-1-BENZOFURAN is utilized as a reagent for the formation of carbon-carbon and carbon-heteroatom bonds, contributing to the synthesis of complex organic compounds.
Used in Material Science:
2-BROMO-1-BENZOFURAN is employed in the development of new materials, taking advantage of its chemical properties to create innovative substances with potential applications in various industries.
Used in Agrochemical Production:
As a precursor in the production of agrochemicals, 2-BROMO-1-BENZOFURAN plays a crucial role in the synthesis of compounds used in agriculture to protect crops and enhance yields.

InChI:InChI=1/C8H5BrO/c9-8-5-6-3-1-2-4-7(6)10-8/h1-5H

Upstream product

• 91703-34-3 2-(β,β-dibromovinyl)phenol 
• 496-41-3 Benzofuran-2-carboxylic acid 
• 613-84-3 2-hydroxy-5-methylbenzaldehyde 
• 98437-24-2 benzofuran-2-boronic acid 
• 1378942-55-2 2-(gem-dibromovinyl)phenol-d 
• 90-02-8 salicylaldehyde 
• 603-33-8 triphenylbismuthane 

Downstream Products

• 496-41-3 Benzofuran-2-carboxylic acid 
• 36724-16-0 2-(methylsulfanyl)benzofuran 
• 4265-27-4 2-n-butylbenzo[b]furan 
• 77234-10-7 2-(2phenylethynyl)benzo[b]furan 
• 1839-72-1 2-phenylbenzofuran 
• 13524-66-8 2-benzyldihydrobenzofuran 
• 4265-14-9 2-benzylbenzofuran 
• 271-89-6 1-benzofurane 
• 13141-47-4 2-propyl-1-benzofuran 
• 28748-41-6 2-(1-methylethyl)benzofuran 
• 19234-04-9 2-(p-methoxyphenyl)-benzo[b]furan 
• 1043252-39-6 2-[(4-methylphenyl)ethynyl]-1-benzofuran 
• 1242137-85-4 2-[(4-fluorophenyl)ethynyl]benzofuran 

Relevant academic research and scientific papers

Palladium-Catalyzed Tandem Synthesis of 2-Trifluoromethylthio(seleno)-Substituted Benzofused Heterocycles

The tandem synthesis of 2-trifluoromethylthio(seleno)-substituted benzofurans using palladium-catalyzed conditions is reported. Trifluoromethylthio(seleno)lation of 2-(2,2-dibromovinyl)phenols with (bpy)CuSCF3 or [(bpy)CuSeCF3]2

Palladium-Catalyzed Domino Cyclization/Phosphorylation of gem-Dibromoolefins with P(O)H Compounds: Synthesis of Phosphorylated Heteroaromatics

We presented a palladium-catalyzed domino cyclization/phosphorylation of gem-dibromoolefins, which utilize H-phosphinates and secondary phosphine oxides as the phosphine sources, respectively. A variety of phosphorylated heteroaromatics were obtained in m

Highly Efficient Synthesis of 2-Substituted Benzo[ b ]furan Derivatives from the Cross-Coupling Reactions of 2-Halobenzo[ b ]furans with Organoalane Reagents

A highly efficient and simple route for the synthesis of 2-substituted benzo[ b ]furans has been developed by palladium-catalyzed cross-coupling reaction of 2-halobenzo[ b ]furans with aryl, alkynyl, and alkylaluminum reagents. Various 2-aryl-, 2-alkynyl-, and 2-alkyl-substituted benzo[ b ]furan derivatives can be obtained in 23-97% isolated yields using 2-3 mol% PdCl 2/4-6 mol% XantPhos as the catalyst under mild reaction conditions. The aryls bearing electron-donating or electron-withdrawing groups in 2-halobenzo[ b ]furans gave products in 40-97% isolated yields. In addition, aluminum reagents containing thienyl, furanyl, trimethylsilanyl, and benzyl groups worked efficiently with 2-halobenzo[ b ]furans as well, and three bioactive molecules with 2-substituted benzo[ b ]furan skeleton were synthesized. Furthermore, the broad substrates scope and the typical maintenance of vigorous efficiency on gram scale make this protocol a potentially practical method to synthesize 2-substituted benzo[ b ]furan derivatives. On the basis of the experimental results, a possible catalytic cycle has been proposed.

Direct bromodeboronation of arylboronic acids with CuBr2 in water

An efficient and practical method has been developed for the preparation of aryl bromides via the direct bromodeboronation of arylboronic acids with CuBr2 in water. This strategy provides several advantages, such as being ligand-free, base-free, high yielding, and functional group tolerant.

Tandem Synthesis of 2-Carboxybenzofurans via Sequential Cu-Catalyzed C-O Coupling and Mo(CO)6-Mediated Carbonylation Reactions

A modular tandem synthesis of 2-carboxybenzofurans from 2-gem-dibromovinylphenols has been established based on a sequence of Cu-catalyzed intramolecular C-O coupling and Mo(CO)6-mediated intermolecular carbonylation reactions. This protocol allowed one-step access to a broad variety of functionalized benzofuran-2-carboxylic acids, esters, and amides in good to excellent yields under Pd- and CO gas-free conditions.

Transition-metal-free decarboxylative bromination of aromatic carboxylic acids

Methods for the conversion of aliphatic acids to alkyl halides have progressed significantly over the past century, however, the analogous decarboxylative bromination of aromatic acids has remained a longstanding challenge. The development of efficient methods for the synthesis of aryl bromides is of great importance as they are versatile reagents in synthesis and are present in many functional molecules. Herein we report a transition metal-free decarboxylative bromination of aromatic acids. The reaction is applicable to many electron-rich aromatic and heteroaromatic acids which have previously proved poor substrates for Hunsdiecker-type reactions. In addition, our preliminary mechanistic study suggests that radical intermediates are not involved in this reaction, which is in contrast to classical Hunsdiecker-type reactivity. Overall, the process demonstrates a useful method for producing valuable reagents from inexpensive and abundant starting materials.

Asymmetric hydrogenation of furans and benzofurans with iridium-pyridine-phosphinite catalysts

Enantioselective hydrogenation of furans and benzofurans remains a challenging task. We report the hydrogenation of 2- and 3-substituted furans by using iridium catalysts that bear bicyclic pyridine-phosphinite ligands. Excellent enantioselectivities and high conversions were obtained for monosubstituted furans with a 3-alkyl or 3-aryl group. Furans substituted at the 2-position and 2,4-disubstituted furans proved to be more difficult substrates. The best results (80-97% conversion, 65-82% enantiomeric excess) were obtained with monosubstituted 2-alkylfurans and 2-[4-(trifluoromethyl)phenyl]furan. Benzofurans with an alkyl substituent at the 2- or 3-position also gave high conversions and enantioselectivity, whereas 2-aryl derivatives showed essentially no reactivity. The asymmetric hydrogenation of a 3-methylbenzofuran derivative was used as a key step in the formal total synthesis of the cytotoxic naphthoquinone natural product (-)-thespesone.

Modulators of methyl modifying enzymes, compositions and uses thereof

Agents for modulating methyl modifying enzymes, compositions and uses thereof are provided herein.

Pd-catalyzed tandem chemoselective synthesis of 2-arylbenzofurans using threefold arylating triarylbismuth reagents

A tandem chemoselective synthesis of 2-arylbenzofurans was accomplished from o-hydroxy-gem-(dibromovinyl)benzenes and BiAr3 reagents under palladium-catalyzed conditions. This unique and synthetically valuable strategy proceeds through three consecutive coupling reactions involving triarylbismuth reagents and provides 2-arylbenzofuran products in high yields. A tandem chemoselective synthesis of 2-arylbenzofurans was accomplished from o-hydroxy-gem-(dibromovinyl)benzenes and BiAr3 reagents under palladium-catalyzed conditions. This unique and synthetically valuable strategy proceeds through three consecutive coupling reactions involving triarylbismuth reagents and provides 2-arylbenzofuran products in high yields. Copyright

Trace amount Cu (ppm)-catalyzed intramolecular cyclization of 2-(gem-dibromovinyl)phenols(thiophenols) to 2-bromobenzofurans(thiophenes)

An intramolecular cyclization of 2-(gem-dibromovinyl)phenols(thiophenols) to give 2-bromobenzofurans(thiophenes) in the presence of a trace amount of Cu (0.0064 mol%, 25 ppm) has been developed. The reaction provides the desired products in excellent yields under fluoride-free and mild reaction conditions and with a TON (turnover number) of up to 1.5 × 104. The Royal Society of Chemistry 2013.