N-bromobutanimide → 1019115-42-4

HRID 2401348Notes

Reaction equation

HRID 2401348 reaction equation
[CH3:1][C:2]1[C:3]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][S:5][C:6]=1[CH3:7].[Br:12]N1C(=O)CCC1=O>CN(C=O)C>[Br:12][C:4]1[S:5][C:6]([CH3:7])=[C:2]([CH3:1])[C:3]=1[C:8]([O:10][CH3:11])=[O:9]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 6397823-Thiophenecarboxylic acid, 4,5-dimethyl-, methyl ester

Product 1

HCID 678127481019115-42-4Yield 94.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 4,5-dimethylthiophene-3-carboxylate (1.89 g, 11.10 mmol) in DMF (10 mL) was added N-bromosuccinimide (2.37 g, 13.32 mmol) at room temperature. The reaction mixture turned orange over time and was allowed to stir for 2 h, at which time LC-MS analysis indicated complete consumption of the methyl 4,5-dimethylthiophene-3-carboxylate. To the solution was added MTBE and water. The aqueous layer was extracted with MTBE (2×), the combined orange organic layer was washed with 1% sodium thiosulfate, followed by water (2×). The organic phase was dried over Na2SO4 and concentrated to give yellow oil. The crude reaction mixture was purified on Biotage system (isocratic elution 2% EtOAc:98% Hexanes) to give the titled compound as a light yellow solid (2.61 g, 10.5 mmol, 94% yield). LC/MS m/z 249 [M+H]+.

Workup

  1. customconsumption of the methyl 4,5-dimethylthiophene-3-carboxylate
  2. additionTo the solution was added MTBE and water
  3. extractionThe aqueous layer was extracted with MTBE (2×)
  4. washthe combined orange organic layer was washed with 1% sodium thiosulfate
  5. dry with materialThe organic phase was dried over Na2SO4
  6. concentrationconcentrated
  7. customto give yellow oil
  8. customThe crude reaction mixture
  9. customwas purified on Biotage system (isocratic elution 2% EtOAc:98% Hexanes)

Sources & evidence

ORD record
ord-f95d5dfbb768464faa06984ce6edc917
Source dataset
uspto-grants-2014_08
Patent number
US08796261B2

Reaction notes

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