Bromine → Methyl 5-bromo-2-methylfuran-3-carboxylate

HRID 9634

Reaction equation

HRID 9634 reaction equation
[Br:1]Br.[CH3:3][C:4]1[O:5][CH:6]=[CH:7][C:8]=1[C:9]([O:11][CH3:12])=[O:10].S([O-])([O-])(=O)=S.[Na+].[Na+]>O1CCOCC1>[Br:1][C:6]1[O:5][C:4]([CH3:3])=[C:8]([C:9]([O:11][CH3:12])=[O:10])[CH:7]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 80237Methyl 2-methylfuran-3-carboxylate

Product 1

HCID 15534190Methyl 5-bromo-2-methylfuran-3-carboxylate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

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.

Workup

  1. stirringStirring
  2. waitat ambient temperature for 18 hours
  3. extractionwas then extracted with ethyl acetate
  4. dry with materialThe organic layer was dried with brine and over magnesium sulfate
  5. customThe product isolated
  6. customafter evaporation of the solvent
  7. customwas further purified by flash column chromatography

Sources & evidence

ORD record
ord-f33b834f86d64fcebdaf4b4e0d91a9c5
Source dataset
uspto-grants-2006_08
Patent number
US07091237B2

Linked notes

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