201412-94-4

Basic information

• Product Name: (Z)-2-Bromo-3-(3,5-dichloro-phenyl)-acrylic acid methyl ester
• CAS NO: 201412-94-4
• Molecular Weight: 309.974
• Mol File: 201412-94-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (Z)-2-Bromo-3-(3,5-dichloro-phenyl)-acrylic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-2-Bromo-3-(3,5-dichloro-phenyl)-acrylic acid methyl ester(201412-94-4)
• EPA Substance Registry System: (Z)-2-Bromo-3-(3,5-dichloro-phenyl)-acrylic acid methyl ester(201412-94-4)

Safety Data

• Hazardous Substances Data: 201412-94-4(Hazardous Substances Data)

Upstream product

• 26631-70-9 cis-2,3-dibromopropenoic acid methyl ester 
• 82297-90-3 3,5-dichlorophenylmagnesium bromide 

Downstream Products

• 201413-06-1 2-[1-(3,5-Dichloro-phenyl)-meth-(E)-ylidene]-4-p-tolyl-but-3-ynoic acid 
• 201413-07-2 (E)-3-(3,5-dichlorophenyl)-2-(1-pentynyl)propenoic acid 
• 201412-98-8 2-[1-(3,5-Dichloro-phenyl)-meth-(E)-ylidene]-4-p-tolyl-but-3-ynoic acid methyl ester 
• 201412-99-9 2-[1-(3,5-Dichloro-phenyl)-meth-(E)-ylidene]-hept-3-ynoic acid methyl ester 

Relevant articles and documents

Studies on the transition metal-catalyzed synthesis of variously substituted (E)-3-[1-(aryl)methylidene]- and (E)-3-(1-alkylidene)-3H-furan-2-ones

5-Aryl and 5-alkyl substituted (E)-3-[1-(aryl)methylidene]- and (E)-3-(1-alkylidene)-3H-furan-2-ones, (E)-9, have been selectively synthesized by cyclization of the corresponding (E)-2-(1-alkynyl)-3-aryl/alkylpropenoic acids, (E)-11, in the presence of AgNO3 or Pd-catalysts such as trans-di(μ-acetato)bis[(di-o-tolylphosphino)benzyl]dipalla-dium(II) or that constituted of a mixture of Et3N and PdCl2(PhCN)2 or PdCl2(CH3CN)2. in a 3:1 molar ratio, respectively. A representative (E)-5-aryl-3-[1-(aryl)methylidene]-3H-furan-2-one, i.e. (E)-9i, has been also prepared by a tandem process involving a Pd(0)- and Cu(I)-catalyzed cross-coupling reaction between an 1-alkyne and a (Z)-3-aryl-2-bromopropenoic acid followed by a catalytic intramolecular oxypalladation of the resulting cross-coupled product. However, when this same approach was used to prepare an (E)-5-alkyl-3-[1-(aryl)methylidene]-3H-furan-2-one, i.e. (E)-9j, a mixture of (E)-9j and the corresponding (E)/(Z)-5-(1-alkylidene)-3-(aryl)methyl-5H-furan-2-one, i.e. (E)/(Z)-20, was obtained. Finally, in an attempt to prepare an (E)-4-alkyl-5-aryl-3-[1-(aryl)methylidene]-3H-furan-2-one, i.e. (E)-14a, by a tandem process involving the intramolecular oxypalladation of an (E)-enynoic acid, (E)-11, followed by a cross-coupling reaction of the resulting compound with aryl iodide, a (Z)-5-(1-alkynyl)-4-aryl-3-arylmethyl-5H-furan-2-one, i.e. (Z)-22, has been stereoselectively obtained.