Iodoethane → Ethyl 3-bromofuran-2-carboxylate
Reaction equation
[Br:1][C:2]1[CH:6]=[CH:5][O:4][C:3]=1[C:7]([OH:9])=[O:8].[CH2:10](I)[CH3:11].C(=O)([O-])[O-].[Cs+].[Cs+].C(=O)([O-])O.[Na+]>C(#N)C>[Br:1][C:2]1[CH:6]=[CH:5][O:4][C:3]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
3-Bromofuran-2-carboxylic acid (1.86 g, 9.75 mmol), ethyl iodide (3.1 mL, 38.8 mol) and cesium carbonate (4.80 g, 14.7 mmol) were suspended in acetonitrile (50 mL), followed by stirring at 80° C. for 3 hours. Aqueous saturated sodium hydrogencarbonate solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure. The resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=9:1), to afford ethyl 3-bromofuran-2-carboxylate (1.16 g, 54%).
Workup
- extractionfollowed by extraction with ethyl acetate
- dry with materialThe organic layer was dried over anhydrous magnesium sulfate
- distillationthe solvent was distilled away under reduced pressure
- customThe resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=9:1)
Sources & evidence
- ORD record
- ord-b10647b73ab34b30a881418443d29dbb
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07718808B2
Reaction notes
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