489423-02-1

Basic information

• Product Name: (E)-tert-butyl{2-methoxy-4-[3-methyl-5-(prop-1-enyl)benzo[b]furan-2-yl]phenoxy}dimethylsilane
• Synonyms: (E)-tert-butyl{2-methoxy-4-[3-methyl-5-(prop-1-enyl)benzo[b]furan-2-yl]phenoxy}dimethylsilane
• CAS NO: 489423-02-1
• Molecular Weight: 408.613
• Mol File: 489423-02-1.mol

Chemical Properties

• CAS DataBase Reference: (E)-tert-butyl{2-methoxy-4-[3-methyl-5-(prop-1-enyl)benzo[b]furan-2-yl]phenoxy}dimethylsilane(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-tert-butyl{2-methoxy-4-[3-methyl-5-(prop-1-enyl)benzo[b]furan-2-yl]phenoxy}dimethylsilane(489423-02-1)
• EPA Substance Registry System: (E)-tert-butyl{2-methoxy-4-[3-methyl-5-(prop-1-enyl)benzo[b]furan-2-yl]phenoxy}dimethylsilane(489423-02-1)

Safety Data

• Hazardous Substances Data: 489423-02-1(Hazardous Substances Data)

Upstream product

• 99660-97-6 dibromo-3,5 benzofuranne 
• 64150-67-0 2,3,5-tribromobenzofuran 
• 568593-05-5 2,3,5-tribromo-2,3-dihydrobenzofuran 
• 123-08-0 4-hydroxy-benzaldehyde 
• 20649-39-2 (E)-1-(4-hydroxyphenyl)propene 
• 489422-91-5 tert-butyl[4-(3,5-dibromobenzo[b]furan-2-yl)-2-methoxyphenoxy]dimethylsilane 
• 149777-72-0 4-Bromo-2-methoxy-1-<(tert-butyldimethylsilyl)oxy>benzene 
• 23145-07-5 5-bromobenzofuran 
• 917-54-4 methyllithium 
• 489422-97-1 {4-[3-bromo-5-(prop-1-enyl)benzo[b]furan-2-yl]-2-methoxyphenoxy}-tert-butyldimethylsilane 

Relevant articles and documents

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.

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.

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