Hydrochloric Acid → Methyl 5-bromo-2-(ethoxymethyl)furan-3-carboxylate

HRID 1877041

Reaction equation

[Br:1][C:2]1[O:6][C:5]([CH2:7]Br)=[C:4]([C:9]([O:11][CH3:12])=[O:10])[CH:3]=1.[O-:13][CH2:14][CH3:15].[Na+].C(O)C.O.Cl>C(O)C>[Br:1][C:2]1[O:6][C:5]([CH2:7][O:13][CH2:14][CH3:15])=[C:4]([C:9]([O:11][CH3:12])=[O:10])[CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of methyl 5-bromo-2-(bromomethyl)furan-3-carboxylate (4.5 g) in ethanol (50 mL) was added 20% sodium ethoxide-ethanol solution (7.8 g) at 0° C., and the mixture was stirred at 0° C. for 2 hr and at room temperature overnight. The reaction was poured into water, and the mixture was acidified with 1N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (0% ethyl acetate/hexane to 15% ethyl acetate/hexane) to give the title compound (2.8 g, 67%) as an oil.

Workup

extractionextracted with ethyl acetate
washThe organic layer was washed with water
dry with materialdried over magnesium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel chromatography (0% ethyl acetate/hexane to 15% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-e39c62e7d8ed4c7787a016bcd89160a4
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08309580B2

Linked notes

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