1222181-90-9

Basic information

• Product Name: (Z)-3-(4-bromophenyl)-5-benzylidene-2,5-dihydrofuran-2-one
• Synonyms: (Z)-3-(4-bromophenyl)-5-benzylidene-2,5-dihydrofuran-2-one
• CAS NO: 1222181-90-9
• Molecular Weight: 327.177
• Mol File: 1222181-90-9.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (Z)-3-(4-bromophenyl)-5-benzylidene-2,5-dihydrofuran-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-3-(4-bromophenyl)-5-benzylidene-2,5-dihydrofuran-2-one(1222181-90-9)
• EPA Substance Registry System: (Z)-3-(4-bromophenyl)-5-benzylidene-2,5-dihydrofuran-2-one(1222181-90-9)

Safety Data

• Hazardous Substances Data: 1222181-90-9(Hazardous Substances Data)

Upstream product

• 148651-39-2 (4-bromophenyl)zinc iodide 
• 208194-66-5 (Z)-5-benzylidene-3-bromo-2,5-dihydrofuran-2-one 

Relevant articles and documents

Two-Step Synthesis of (Z)-3-Aryl-5-(arylmethylidene)butenolides by an Ivanov Reaction/Silver(I)-Catalyzed Lactonization/In Situ Dehydration Sequence

A stereoselective synthesis of the title compounds was developed. Hexane- and amine-free THF solutions of α-lithiated lithium arylacetates ('arylacetic acid dianions') were aldol-added to 3-arylpropynals. This gave 2,5-diaryl-3-hydroxypent-4-ynoic acids with up to a 72:28 preference for the anti-diastereomer (27 examples + 1 exception). When treated with Ag2CO3 (1-20 mol%) in DMF at room temperature for 2.5 days, the respective mixtures underwent regio- and stereoselective lactonizations followed by an in situ dehydration. Thereby 3-aryl-5-(arylmethylidene)butenolides were obtained with a Z-configuration of the oxygenated C=C bond. Their overall yields ranged from 46% to 83% (1 exception: 28%). Three 3-aryl-5-(arylmethylidene)butenolides contained a C-Br and/or a C-I bond. They allowed a subsequent Pd-catalyzed C-C coupling, which furnished follow-up butenolides.