41744-28-9

Usage

InChI:InChI=1/C19H18O3/c1-4-5-13-6-9-17-15(10-13)12(2)19(22-17)14-7-8-16(20)18(11-14)21-3/h4-11,20H,1-3H3/b5-4+

Upstream product

• 23145-07-5 5-bromobenzofuran 
• 99660-97-6 dibromo-3,5 benzofuranne 
• 64150-67-0 2,3,5-tribromobenzofuran 
• 568593-05-5 2,3,5-tribromo-2,3-dihydrobenzofuran 
• 149777-72-0 4-Bromo-2-methoxy-1-<(tert-butyldimethylsilyl)oxy>benzene 
• 489422-91-5 tert-butyl[4-(3,5-dibromobenzo[b]furan-2-yl)-2-methoxyphenoxy]dimethylsilane 
• 489422-97-1 {4-[3-bromo-5-(prop-1-enyl)benzo[b]furan-2-yl]-2-methoxyphenoxy}-tert-butyldimethylsilane 
• 56681-66-4 3-methoxy-4-acetoxybenzoyl chloride 
• 10543-12-1 4-acetoxy-3-methoxybenzoic acid 
• 121-34-6 3-methoxy-4-hydroxybenzoic acid 
• 86253-65-8 2-ethyl-4-propyl 4-acetoxy-3-methoxybenzoate 
• 86253-66-9 4-Acetoxy-3-methoxy-benzoic acid 2-(1-bromo-ethyl)-4-(1-bromo-propyl)-phenyl ester 
• 20649-39-2 (E)-1-(4-hydroxyphenyl)propene 
• 123-08-0 4-hydroxy-benzaldehyde 

Downstream Products

• 41744-29-0 (E)-2-(3,4-dimethoxyphenyl)-3-methyl-5-(prop-1-enyl)benzo[b]furan 

Relevant academic research and scientific papers

Practical, modular, and general synthesis of benzofurans through extended pummerer annulation/cross-coupling strategy

Operationally simple, efficient, and widely applicable Pummerer annulations of simple phenols with ketene dithioacetal monoxides, with the aid of trifluoroacetic anhydride, have been shown to provide a variety of benzofurans having a methylthio group at the 2-position. Subsequent and newly developed nickel-catalyzed arylation at the methylthio group culminates in diversity-oriented synthesis of multisubstituted benzofurans. Our extended Pummerer annulation/cross-coupling sequence is powerful enough to synthesize biologically active natural products as well as highly fluorescent benzofuran derivatives.

Two-step, practical, and diversity-oriented synthesis of multisubstituted benzofurans from phenols through Pummerer annulation followed by cross-coupling

Practical and diversity-oriented synthesis of multisubstituted benzofurans has been accomplished from simple phenols through a Pummerer annulation/cross-coupling sequence. Operationally simple and rapid reactions of phenols with ketene dithioacetal monoxides (KDMs) with the aid of trifluoroacetic anhydride provide the corresponding 2-methylsulfanylbenzo[b]furans. The scope of the reaction encompasses phenols and KDMs having a broad range of substituents. The remaining methylsulfanyl group in the annulation products is converted to various aryl groups through cross-coupling reactions that we improved specially to this end. This two-step approach to multisubstituted benzofurans is powerful enough to synthesize highly fluorescent benzofuran derivatives as well as the naturally occurring Eupomatenoid family.

Regioselective C-C bond formation reactions on 2,3-dibromo- and 2,3,5-tribromobenzofuran as an access to multiply substituted benzofurans. Total syntheses of eupomatenoids 3, 4, 5, 6, and 15

Regioselective C-C-bond formation reactions at 2,3-dibromobenzofuran (1) and 2,3,5-tribromobenzofuran (6) were studied. Pd-catalyzed Sonogashira and Negishi cross-coupling occurred with perfect regioselectivity at carbon atom C-2 to provide 2-substituted 3-bromobenzofurans (12, 14) and 3,5-dibromobenzofurans (17, 18) in 50-91% yield. A regioselective displacement of the bromine substituents in 3,5-dibromobenzofurans 18 was achieved by a halogen-metal exchange reaction at carbon atom C-3 and by a Nicatalyzed Kumada cross-coupling at C-5. The methodology was applied to the synthesis of eupomatenoids 3, 4, 5, 6, and 15 (5). The synthesis of these compounds was achieved in overall yields of up to 60%.

Synthesis of eupomatenoids by three consecutive transition metal-catalyzed cross-coupling reactions

Six different eupomatenoids (1a-c, 1f-h) were prepared from 2,3,5-tribromobenzofuran (2) in a concise and high-yielding synthetic sequence. The overall yields vary between 29 and 60% over four to six steps. Key to the success of the syntheses is the high

Natural Benzofuranes. Synthesis of Eupomatenoids-1, -3, -4, -5, -6, -7, and -13

A group of eupomatenoids, natural lignans possessing 2-aryl-3-methyl-5-propenylbenzofuran structures have been synthesized by short pathways which include the intramolecular Wittig reaction of an o-bromoethylaryl benzoate ester as a key step.