N-bromobutanimide → 2-bromo-4H,5H,6H-thieno(2,3-c)pyrrol-6-one

HRID 1921820Notes

Reaction equation

HRID 1921820 reaction equation
[S:1]1[C:5]2[C:6](=[O:9])[NH:7][CH2:8][C:4]=2[CH:3]=[CH:2]1.C1C(=O)N([Br:17])C(=O)C1>C(#N)C>[Br:17][C:2]1[S:1][C:5]2[C:6](=[O:9])[NH:7][CH2:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 205428054H,5H,6H-thieno[2,3-c]pyrrol-6-one

Product 1

HCID 590231412-bromo-4H,5H,6H-thieno(2,3-c)pyrrol-6-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4,5-Dihydro-thieno[2,3-c]pyrrol-6-one (0.365 g, 2.63 mmol) is dissolved in acetonitrile (10 mL), and NBS (0.47 g, 2.63 mmol) is slowly added at −10° C. The reaction mixture is stirred at room temperature overnight. The solvent is removed in vacuo and the residue taken-up in EtOAc and washed with 1M NaOH. The organic phase is dried over MgSO4, filtered and concentrated in vacuo. The crude is purified by silica gel column chromatography eluting with a 50:50 mixture and then 50:70 petroleum ether-EtOAc. The title compound is isolated (91.1 mg, 16%). HPLC (254 nm): Rt 2.55 min (70.3%), m/z 218/220 (M+H)+.

Workup

  1. customThe solvent is removed in vacuo
  2. washthe residue taken-up in EtOAc and washed with 1M NaOH
  3. dry with materialThe organic phase is dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude is purified by silica gel column chromatography
  7. washeluting with a 50:50 mixture

Sources & evidence

ORD record
ord-25f33f57b63b40c392bd8ad9b5d2e7da
Source dataset
uspto-grants-2012_05
Patent number
US08173656B2

Reaction notes

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