38527-59-2

Usage

Structure

Furan derivative with a furan ring and a methoxyphenyl group attached at position 2

Appearance

Colorless to pale yellow liquid

Odor

Sweet, floral

Usage

Synthesis of pharmaceuticals, agrochemicals, flavor and fragrance industry

Value

Valuable building block for production of compounds with pharmaceutical and aromatic applications

Upstream product

• 5720-06-9 2-Methoxyphenylboronic acid 
• 110-00-9 furan 
• 6165-76-0 propargyl p-toluenesulfonate 
• 578-57-4 2-bromoanisole 
• 584-12-3 2-bromofuran 
• 16750-63-3 2-methoxyphenylmagnesium bromide 
• 118486-94-5 2-(tributylstannyl)furan 
• 529-28-2 4-iodoanisol 

Downstream Products

• 106584-14-9 2-(2-Furyl)phenol 

Relevant academic research and scientific papers

Synthesis method of monosubstituted or disubstituted furan derivatives

The invention relates to the field of medicine synthesis, and provides a synthesis method of monosubstituted or disubstituted furan derivatives, wherein the synthesis method can be used for synthesizing various furan derivatives with different substituent groups and has high flexibility. According to the synthesis method of the monosubstituted or disubstituted furan derivatives, 5-hydroxymethyl-[delta]2-isoxazoline derivative is used as a raw material in an acidic solvent, and the monosubstituted or disubstituted furan derivatives are synthesized in one step under the action of a metal reducing agent; and according to the method, the furan derivatives with different substituent groups can be synthesized by adopting the 5-hydroxymethyl-[delta]2-isoxazoline derivatives with different substituent groups, high flexibility is achieved, the technical scheme is simple in step and mild in reaction condition, synthesis of the furan derivatives can be achieved through a one-pot method, the reaction yield is high, and large-scale production is facilitated.

Stille couplings in water at room temperature

A nonionic amphiphile, TPGS-750-M, enables efficient Stille couplings between a wide range of substrates to be conducted in water as the only medium, in most cases at room temperature.

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.

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.

A re(V)-catalyzed C-N bond-forming route to human lipoxygenase inhibitors

(Chemical Equation Presented) A regioselective synthesis of propargylamines by the coupling of propargyl alcohols with tosylamines and carbamates catalyzed by an air-and moisture-tolerant rhenium-oxo complex is described. The ability to couple functionali

Preparation of furans by palladium-catalyzed reaction of acylchromates and propargylic tosylates

Substituted furans are prepared by the palladium-catalyzed reaction of propargylic tosylates with acylchromates. The reaction is initiated by the oxidative additiion of propagylic tosylates to palladium(O) complexes to give 1,2-propadienylpalladium(II) co

Generation of aryl radicals from arylboronic acids by manganese(III) acetate: Synthesis of biaryls and heterobiaryls

The efficient generation of aryl radicals from arylboronic acids by manganese(III) acetate is described. In aromatic solvents, in situ generated aryl radicals afford the corresponding biaryls in very good yields. This method works selectively, and yields

α1-Adrenoceptor agonists: The identification of novel α1A subtype selective 2′-heteroaryl-2-(phenoxymethyl)imidazolines

Novel 2′-heteroaryl-2-(phenoxymethyl)imidazolines have been identified as potent agonists of the cloned human α1-adrenoceptors in vitro. The nature of the 2′-heteroaryl group can have significant effects on the potency, efficacy, and subtype selectivity in this series. α1A Subtype selective agonists have been identified.