329328-49-6

Basic information

• Product Name: 2(5H)-Furanone, 3-bromo-4-[4-(methylthio)phenyl]-
• CAS NO: 329328-49-6
• Molecular Formula: C11H9BrO2S
• Molecular Weight: 285.161
• Mol File: 329328-49-6.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2(5H)-Furanone, 3-bromo-4-[4-(methylthio)phenyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: 2(5H)-Furanone, 3-bromo-4-[4-(methylthio)phenyl]-(329328-49-6)
• EPA Substance Registry System: 2(5H)-Furanone, 3-bromo-4-[4-(methylthio)phenyl]-(329328-49-6)

Safety Data

• Hazardous Substances Data: 329328-49-6(Hazardous Substances Data)

Upstream product

• 149418-41-7 3,4-dibromo-2(5H)-furanone 
• 98546-51-1 (4-thiomethoxyphenyl)boronic acid 
• 17113-79-0 trimethyl(4-(methylthio)phenyl)stannane 

Downstream Products

• 162012-30-8 4-(4-(methylthio)phenyl)-3-phenylfuran-2(5H)-one 
• 162011-90-7 rofecoxib 
• 866336-10-9 thiobutyric acid S-[4-(5-oxo-4-phenyl-2,5-dihydro-furan-3-yl)-phenyl] ester 
• 745820-44-4 4-(4-(methylsulfinyl)phenyl)-3-phenylfuran-2(5H)-one 
• 487047-31-4 3-chloro-4-(4'-methylsulfonylphenyl)-5H-furan-2-one 
• 162012-28-4 4-(4-(methylthio)phenyl)furan-2(5H)-one 

Relevant articles and documents

Preparation of aryl-substituted butenolides using mucohalic acids

Methods and materials for preparing 3-aryl-2-buten-4-olides and 2,3-bisaryl-2-buten-4-olides are disclosed. The methods include reacting a mucohalic acid with a reducing agent to give a 2,3-dihalo-2-buten-4-olide, which undergoes at least one Pd catalyzed cross-coupling reaction with an arylboronic acid.

Reinvestigation of mucohalic acids, versatile and useful building blocks for highly functionalized alpha,beta-unsaturated gamma-butyrolactones.

[reaction: see text] Mucohalic acids (mucochloric acid (1, 3,4-dichloro-5-hydroxy-5H-furan-2-one) and mucobromic acid (2, 3,4-dibromo-5-hydroxy-5H-furan-2-one)) are inexpensive, commercially available starting materials with multiple functional groups. These compounds have been modified by way of reduction followed by Suzuki cross-coupling reactions involving arylboronic acids to afford highly functionalized alpha,beta-unsaturated gamma-butyrolactones in excellent yield. The synthetic utility of these building blocks was effectively demonstrated through preparation of the antiinflammatory drug Vioxx.

Selective synthesis of unsymmetrical 3,4-disubstituted and 4-substituted 2(5H)-furanones

Easily available 3,4-dibromo-2(5H)-furanone undergoes regioselective palladium-catalyzed reaction with aryl(trialkyl)stannanes to give the corresponding 4-aryl-3-bromo-2(5H)-furanones in satisfactory yields. These monobromo derivatives have proven to be useful precursors to unsymmetrical 3,4-diaryl-2(5H)-furanones, 4-aryl-3-methyl-2(5H)-furanones and 4-aryl-2(5H)-furanones.