Iodoethane → Ethyl 3-bromofuran-2-carboxylate

HRID 337546

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

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-a3b9f2d876214edcbe0ca512f91496f6
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889718B2

Linked notes

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