Water → Methyl 5-bromo-2-methylfuran-3-carboxylate

HRID 1876970Notes

Reaction equation

HRID 1876970 reaction equation
[CH3:1][C:2]1[O:3][CH:4]=[CH:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8].[Br:11]N1C(=O)CCC1=O.O>CN(C)C=O>[Br:11][C:4]1[O:3][C:2]([CH3:1])=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 80237Methyl 2-methylfuran-3-carboxylate

Product 1

HCID 15534190Methyl 5-bromo-2-methylfuran-3-carboxylateYield 72.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 2-methyl-3-furoate (7.0 g) in N,N-dimethylformamide (50 mL) was added N-bromosuccinimide (10.7 g) over 45 min under ice-cooling, and the mixture was stirred under ice-cooling for 30 min and at room temperature overnight. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was collected, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (0% ethyl acetate/hexane to 5% ethyl acetate/hexane) to give the title compound (7.9 g, 72%) as an oil.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. customThe organic layer was collected
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (0% ethyl acetate/hexane to 5% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-4e2b1e1d6bdb4830a7bcff00c0879cb2
Source dataset
uspto-grants-2012_11
Patent number
US08309580B2

Reaction notes

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