Reaction #9730

Reaction equation

Bromine

methyl 2-methyl-3-furancarboxylate

sodium thiosulfate

→

title compound

methyl 5-bromo-2-methyl-3-furoate

Solvents

1,4-dioxane

Conditions

Workup

1. 1
   workup.STIRRINGStirring
2. 2
   workup.WAITat ambient temperature for 18 hours
3. 3
   Extractionwas then extracted with ethyl acetate
4. 4
   DryingThe organic layer was dried with brine and over magnesium sulfate
5. 5
   OtherThe product isolated
6. 6
   Otherafter evaporation of the solvent
7. 7
   Otherwas further purified by flash column chromatography

Procedure

Bromine (2.0 ml) was added drop-wise to a mixture of methyl 2-methyl-3-furancarboxylate (5.0 g) in 1,4-dioxane (35 ml) stirred at 0° C. Stirring was continued at 0° C. for 2 hours and then at ambient temperature for 18 hours. Saturated aqueous sodium thiosulfate was added to the reaction mixture which was then extracted with ethyl acetate. The organic layer was dried with brine and over magnesium sulfate. The product isolated after evaporation of the solvent was further purified by flash column chromatography using cyclohexane:ethyl acetate (19:1) as eluent to give the title compound as a yellow oil.

Source