Water → Methyl 5-bromo-2-[(methylsulfanyl)methyl]furan-3-carboxylate

HRID 1877171Notes

Reaction equation

HRID 1877171 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][S-:14].[Na+].O>O1CCCC1>[Br:1][C:2]1[O:6][C:5]([CH2:7][S:14][CH3:13])=[C:4]([C:9]([O:11][CH3:12])=[O:10])[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4378561Sodium methanethiolateHCID 15534191Methyl 5-bromo-2-(bromomethyl)furan-3-carboxylate

Product 1

HCID 68516524Methyl 5-bromo-2-[(methylsulfanyl)methyl]furan-3-carboxylateYield 84.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 5-bromo-2-(bromomethyl)furan-3-carboxylate (8.9 g) in tetrahydrofuran (50 mL) was added sodium methanethiolate (2.5 g) at 0° C., and the mixture was stirred overnight at room temperature. The reaction mixture was poured into water, and the mixture was 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 10% ethyl acetate/hexane) to give the title compound (6.7 g, 84%) as an oil.

Workup

  1. extractionthe mixture was extracted 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 10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-ddbb80085a534c58a8e6a182117749c6
Source dataset
uspto-grants-2012_11
Patent number
US08309580B2

Reaction notes

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