13141-26-9

Usage

Uses

Used in Organic Synthesis:
Benzofuran, 5-bromo-2-phenyl-, is used as a building block in organic synthesis for the creation of various biologically active compounds. Its unique structure and reactivity make it a valuable component in the development of new organic compounds.
Used in Pharmaceutical Research:
In pharmaceutical research, Benzofuran, 5-bromo-2-phenyl-, is employed as a key intermediate in the synthesis of pharmaceuticals. Its potential applications in antipsychotic and anticancer treatments are being investigated, highlighting its importance in the development of new medications.
Used as a Research Tool:
Benzofuran, 5-bromo-2-phenyl-, also serves as a research tool in the study of chemical and biological processes. Its unique properties and reactivity allow researchers to gain insights into various aspects of chemistry and biology, furthering scientific understanding and innovation.

Upstream product

• 207115-22-8 4-bromo-2-iodophenol 
• 536-74-3 phenylacetylene 
• 1135146-47-2 C₁₇H₁₉BrO₂Si 
• 1261815-96-6 2-(5-bromo-2-hydroxyphenyl)acetonitrile 
• 23145-07-5 5-bromobenzofuran 
• 98-09-9 benzenesulfonyl chloride 
• 22596-45-8 2-methyl-2-nitro-3-phenyloxirane 
• 1761-61-1 5-bromosalicyclaldehyde 
• 705-60-2 (2-nitroprop-1-enyl)benzene 
• 4755-72-0 Chloro-phenyl-acetic acid 
• 56280-66-1 diethyl(phenyl)aluminium 
• 100-58-3 phenylmagnesium bromide 
• 1191415-07-2 4-bromo-2-(2,2-dibromovinyl)phenol 
• 100-42-5 styrene 

Downstream Products

• 121045-39-4 5-methyl-2-phenylbenzofuran 
• 1052726-93-8 5-bromo-3-(2-chloroacetyl)-2-phenylbenzo[b]furan 

Relevant academic research and scientific papers

Palladium-catalyzed tandem reaction of 2-hydroxyarylacetonitriles with sodium sulfinates: One-pot synthesis of 2-arylbenzofurans

The first example of the palladium-catalyzed one-pot synthesis of 2-arylbenzofurans in moderate to excellent yields via a tandem reaction of 2-hydroxyarylacetonitriles with sodium sulfinates is reported. A plausible mechanism for the formation of 2-arylbenzofurans involving desulfinative addition and intramolecular annulation reactions is proposed. Moreover, the present synthetic route to benzofurans could be readily scaled up to the gram quantity without any difficulty. Thus, the method represents a convenient and practical strategy for synthesis of benzofuran derivatives. This journal is the Partner Organisations 2014.

Acid-promoted selective synthesis of trifluoromethylselenolated benzofurans with Se-(trifluoromethyl) 4-methylbenzenesulfonoselenoate

A Br?nsted acid-promoted trifluoromethylselenolation of benzofurans was disclosed by using Se-(trifluoromethyl) 4-methylbenzenesulfonoselenoate as a stable and easily prepared electrophilic trifluoromethylselenolating reagent. A wide range of SeCF3-substituted benzofuran derivatives were obtained in moderate to good yields with excellent regioselectivity. The tandem cyclization/trifluoromethylselenolation procedure of 1-methoxy-2-(arylethynyl)benzenes were also realized by engaging FeCl3 as the catalyst.

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.

Catalyst-Free Synthesis of Benzofuran Derivatives from Cascade Reactions between Nitroepoxides and Salicylaldehydes

Different benzofuran derivatives are synthesized via a catalyst-free reaction between nitroepoxides and salicylaldehydes. In the employed methodology, K2CO3 and DMF have been used at 110 °C, and the reactions were completed after 12 h in 33-84% yields. Th

Arylation synthesis method for novel five-membered aromatic heterocycle and aromatic-ring five-membered aromatic heterocycle

The invention belongs to the technical field of organic synthesis and in particular relates to an arylation synthesis method for a five-membered aromatic heterocycle or an aromatic-ring five-memberedaromatic heterocycle under the participation of an arylhydrazine derivative serving as a novel arylation reagent. The method comprises the steps: adding a raw material and aroyl hydrazine into a reactor, and carrying out a reaction at 60-100 DEG C for 8-24h under the condition that an oxidant and a transition metal catalyst are added; after the reaction is ended, carrying out suction filtration, extracting a filtrate by using ethyl acetate, carrying out drying to obtain a crude product of a target compound, and carrying out column chromatography on silica gel to obtain a pure product of the target compound. The arylation synthesis method for the five-membered aromatic heterocycle or the aromatic-ring five-membered aromatic heterocycle is scientific and reasonable and has the advantages such as simplicity and convenience in operation, relatively high yield and simplicity in amplification and purification.

Mechanistic Insights on Orthogonal Selectivity in Heterocycle Synthesis

Recently, we have developed a method for catalytic regioselective synthesis of 2-substituted and 3-substituted benzofurans starting from phenols. The choice of reacting partner, olefin versus α,β-unsaturated acid, is critical to dictate the isomeric product formation. Instances are known where these olefinic partners did not complement each other and yield a similar outcome. In the current work, we have addressed this paradox with emphasis on (a) the origin of orthogonal selectivity and (b) the key requirements to expect complementary behavior. Experimental and computational studies provided important mechanistic insights. Electrostatic compatibility during migratory insertion and the positioning of the carboxylic acid moiety in catalytic steps are found to exert a paramount impact in determining the regioselectivity. The study offers a predictable single component tuning tool to control the regioselectivity.

Indium(III)-Catalyzed Synthesis of Benzo[ b]furans by Intramolecular Hydroalkoxylation of ortho-Alkynylphenols: Scope and Mechanistic Insights

Indium(III) halides catalyze the hydroalkoxylation reaction of ortho-alkynylphenols to afford benzo[b]furans in good yields. The reaction proceeds with 5-endo-dig regioselectivity with a variety of phenols functionalized at the arene and alkyne moieties in high yields using InI3 (5 mol %) in DCE. Experimental and computational studies support a mechanism based on the indium(III) π-Lewis acid activation of the alkyne followed by nucleophilic addition of the phenol and final protodemetalation to afford the corresponding benzo[b]furan. DFT calculations suggest that dimer In2I6 is the catalytic species through a novel double coordination with the alkyne and the hydroxyl group.

Palladium-Catalyzed Regioselective C-2 Arylation of Benzofurans with N′-Acyl Arylhydrazines

A novel ligand-free palladium-catalyzed C-2 arylation of benzofurans has been developed using N′-acyl arylhydrazines as the coupling partners and TEMPO as an oxidant. This protocol features a wide functional-group tolerance and highly regioselective products with good to excellent yields.

Strategy for Overcoming Full Reversibility of Intermolecular Radical Addition to Aldehydes: Tandem C-H and C-O Bonds Cleaving Cyclization of (Phenoxymethyl)arenes with Carbonyls to Benzofurans

An intermolecular addition of carbon radicals enabled by a cascade radical coupling strategy is developed. It includes an intermolecular alkyl radical addition to a carbonyl group followed by an intramolecular alkoxy radical addition to haloarenes and produces substituted benzofurans in high yields. The radical nature of this reaction is explored by radical trapping experiments and EPR analysis. The mechanism is investigated by KIE experiments and control experiments. This method could provide rapid and practical access to the key intermediate of TAM-16, a safe and potent antibacterial agent for treating tuberculosis, and, therefore, is of great importance for organic synthesis and the pharmaceutical industry.

Aerobic, Metal-Free, and Catalytic Dehydrogenative Coupling of Heterocycles: En Route to Hedgehog Signaling Pathway Inhibitors

The nitrosonium ion-catalyzed dehydrogenative coupling of heteroarenes under mild reaction conditions is reported. The developed method utilizes ambient molecular oxygen as a terminal oxidant, and only water is produced as byproduct. Dehydrogenative coupl