Hydrochloric Acid → Methyl 5-bromo-2-(methoxymethyl)-3-furancarboxylate

HRID 1877038Notes

Reaction equation

HRID 1877038 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.[CH3:13][O-:14].[Na+].O.Cl>CO>[Br:1][C:2]1[O:6][C:5]([CH2:7][O:14][CH3:13])=[C:4]([C:9]([O:11][CH3:12])=[O:10])[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 10942334Sodium MethoxideHCID 15534191Methyl 5-bromo-2-(bromomethyl)furan-3-carboxylate

Product 1

HCID 68509863Methyl 5-bromo-2-(methoxymethyl)-3-furancarboxylateYield 77%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 5-bromo-2-(bromomethyl)furan-3-carboxylate (3.0 g) in methanol (30 mL) was added sodium methoxide (0.8 g) at 0° C., and the mixture was stirred at room temperature overnight. The reaction mixture 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 20% ethyl acetate/hexane) to give the title compound (1.9 g, 77%) as an oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel chromatography (0% ethyl acetate/hexane to 20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-3db0976ca935482bae453c50e5a37359
Source dataset
uspto-grants-2012_11
Patent number
US08309580B2

Reaction notes

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