Iodoethane → Ethyl 3-bromofuran-2-carboxylate

HRID 1361899

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-d5bfc4c465ad4b3bbd3874a6474ffd1b
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07880013B2

Linked notes

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