35461-93-9

Usage

Uses

Used in Pharmaceutical Applications:
2-(3-Methoxy phenyl)furan is used as a starting material in the synthesis of various biologically active compounds, particularly those with pharmaceutical applications. Its antioxidant and anti-inflammatory properties have been reported, and it has been studied for its potential therapeutic effects.
Used in Organic Chemistry:
2-(3-Methoxy phenyl)furan is used as a key intermediate in the preparation of complex organic molecules, contributing to the advancement of organic chemistry.
Used in Organic Electronics:
2-(3-Methoxy phenyl)furan is used in the development of new materials for organic electronics due to its unique chemical and physical properties, which can enhance the performance of electronic devices.
Used in Optoelectronic Devices:
2-(3-Methoxy phenyl)furan is used in the creation of materials for optoelectronic devices, where its properties can improve the efficiency and functionality of these devices.

Upstream product

• 110-00-9 furan 
• 2398-37-0 3-methoxyphenyl bromide 
• 2786-02-9 2-lithiofuran 
• 98910-57-7 2-methoxyphenyl mesylate 
• 155586-44-0 1-(3-methoxyphenyl)buta-2,3-dien-1-one 
• 10365-98-7 3-methoxyphenylboronic acid 
• 584-12-3 2-bromofuran 
• 2845-89-8 1-chloro-3-methoxy-benzene 
• 36282-40-3 (3-methoxyphenyl)magnesium bromide 
• 53290-32-7 m-MeOC₆H₄NMe₃(+)*I(-) 
• 81745-86-0 2-furylzinc chloride 
• 325142-84-5 3-methoxyphenylboronic acid pinacol ester 
• 13331-23-2 fur-2-ylboronic acid 
• 1527-89-5 3-methoxybenzonitrile 

Downstream Products

• 111853-63-5 5-(3-Methoxy-phenyl)-3H-furan-2-one 

Relevant academic research and scientific papers

Transition-Metal-Free Synthesis of Heterobiaryls through 1,2-Migration of Boronate Complex

The synthesis of a diverse range of heterobiaryls has been achieved by a transition-metal-free sp2–sp2 cross-coupling strategy using lithiated heterocycle, aryl or heteroaryl boronic ester and an electrophilic halogen source. The construction of heterobiaryls was carried out through electrophilic activation of the aryl–heteroaryl boronate complex, which triggered 1,2-migration from boron to the carbon atom. Subsequent oxidation of the intermediate boronic ester afforded heterobiaryls in good yield. A comprehensive 11B NMR study has been conducted to support the mechanism. The cross coupling between two nucleophilic cross coupling partners without transition metals reveals a reliable manifold to procure heterobiaryls in good yields. Various heterocycles like furan, thiophene, benzofuran, benzothiophene, and indole are well tolerated. Finally, we have successfully demonstrated the gram scale synthesis of the intermediates for an anticancer drug and OLED material using our methodology.

Synthesis of 2,5-Disubstituted Furans from Sc(OTf)3 Catalyzed Reaction of Aryl Oxiranediesters with γ-Hydroxyenones

A convenient synthesis of 2,5-disubstituted furan was developed by employing donor-acceptor oxiranes in a new reaction with γ-hydroxyenones. Sc(OTf)3 was found to be the best catalyst, and 2,5-disubstituted furans are obtained in moderate to good yields under mild reaction conditions. The scope of the reaction is quite decent, allowing for the synthesis of disubstituted furans having aryl and heteroaromatic groups.

Sodium Chloride Catalyzed Regioselective Trifluoromethylthiolation of Furans

Here, we report the catalytic trifluoromethylthiolation of furans employing sodium chloride as an inexpensive, abundant and ecologically friendly catalyst. The developed method exhibits perfect regioselectivity and a high functional group tolerance. Furth

Unexpected dual role of titanium dioxide in the visible light heterogeneous catalyzed C-H arylation of heteroarenes

The direct arylation of heteroaromatics with an easily accessible and recyclable, heterogeneous TiO2 catalyst and visible light was developed. Electron-rich as well as electron-poor heteroarenes could be applied in this transformation, and the corresponding products were isolated in very good yields. Azoethers were detected as reactive intermediates, and the unexpected role of TiO2 in their formation as well as reaction was established.

Nickel-catalyzed cross-coupling of arene-or heteroarenecarbonitriles with aryl-or heteroarylmanganese reagents through C-CN bond activation

The nickel-catalyzed cross-coupling reaction of arene- or heteroarenecarbonitriles with aryl- or heteroarylmanganese reagents via C-CN bond activation has been developed. Both electron-rich and electron-deficient nitriles can be employed as the electrophilic substrates. The reaction tolerates a range of functional groups and aromatic heterocycles. Copyright

Cross-coupling of aryltrimethylammonium iodides with arylzinc reagents catalyzed by amido pincer nickel complexes

The cross-coupling reaction of aryltrimethylammonium iodides with aryl- or heteroarylzinc chlorides catalyzed by amido pincer nickel complexes was performed. The reaction requires low catalyst loading and displays broad substrate scope.

Synthesis of 2-substituted furans by iron- and palladium-catalyzed coupling reactions

The synthesis of 2-substituted furans via palladium- and iron-catalyzed coupling utilizing 2-bromofuran is described. Whereas palladium-catalyzed Suzuki coupling effectively provided the corresponding aryl furans, little or no product was obtained by palladium-catalyzed coupling with various alkyl nucleophiles. Iron-catalyzed coupling proved effective for the synthesis of primary and secondary alkyl furans in modest yields and aryl furans in low yields. Georg Thieme Verlag Stuttgart New York.

Palladium-catalyzed indole, pyrrole, and furan arylation by aryl chlorides

The palladium-catalyzed direct arylation of indoles, pyrroles, and furans by aryl chlorides has been demonstrated. The method employs a palladium acetate catalyst, 2-(dicyclohexylphosphino)-biphenyl ligand, and an inorganic base. Electron-rich and electron-poor aryl chlorides as well as chloropyridine coupling partners can be used, and arylated heterocycles are obtained in moderate to good yields. Optimization of base, ligand, and solvent is required for achieving best results.

Efficient procedure for the preparation of 2-bromofuran and its application in the synthesis of 2-arylfurans

A simple, straightforward, and scalable procedure for the preparation of 2-bromofuran using N-bromosuccinimide (NBS) in dimethylformamide (DMF) is reported. The described preparation is conducted on a 20 to 50g scale and does not require extractive workup procedures or chromatographic purifications. To illustrate the synthetic applications of 2-bromofuran, palladium-catalyzed Suzuki coupling reactions of the prepared 2-bromofuran with various aryl boronic acids were investigated, and moderate to good yields of 2-arylfurans were obtained. Copyright Taylor & Francis Group, LLC.

Deprotonative metalation of functionalized aromatics using mixed lithium-cadmium, lithium-indium, and lithium-zinc species

In situ mixtures of CdCl2TMEDA (0.5 equiv; TMEDA = N,N,N',N'-tetramethylethylenediamine) or InCl3 (0.33 equiv) with [Li(tmp)] (tmp = 2,2,6,6-tetramethylpiperidino; 1.5 or 1.3 equiv, respectively) were compared with the previously described mixture of ZnCl2-TMEDA (0.5 equiv) and [Li(tmp)] (1.5 equiv) for their ability to deprotonate anisole, benzothiazole, and pyrimidine. [(tmp)3CdLi] proved to be the best base when used in tetrahydrofuran at room temperature, as demonstrated by subsequent trapping with iodine. The Cd-Li base then proved suitable for the metalation of a large range of aromatics including benzenes bearing reactive functional groups (CONEt2, CO2Me, CN, COPh) or heavy halogens (Br, I), and heterocycles (from the furan, thiophene, pyrrole, oxazole, thiazole, pyridine, and diazine series). Fivemembered heterocycles benefiting from doubly activated positions were similarly dideprotonated at room temperature. The aromatic lithium cadmates thus obtained were involved in palladium-catalyzed cross-coupling reactions or simply quenched with acid chlorides.