Acetonitrile → 1-(2-Bromoethyl)pyrrolidine-2,5-dione
Reaction equation
[O:1]1[C:5](=[O:6])[CH2:4][CH2:3][C:2]1=O.[Br:8][CH2:9][CH2:10]Br.C([O-])([O-])=O.[K+].[K+].CC#[N:20]>>[Br:8][CH2:9][CH2:10][N:20]1[C:2](=[O:1])[CH2:3][CH2:4][C:5]1=[O:6]Participants
5
Procedure
To a mixture of dihydro-furan-2,5-dione (396 mg, 4.00 mmol) and 1,2-dibromo-ethane (1.50 g, 8.00 mmol) in CH3CN (20 ml) was added K2CO3 (829 mg, 6.00 mmol) at room temperature. The mixture was stirred at reflux overnight and the solvent was evaporated. The mixture was diluted with EtOAc (150 mL), washed with water, sat. Na2CO3aq., brine, and dried over MgSO4. The solvent was evaporated to give 1-(2-bromo-ethyl)-pyrrolidine-2,5-dione that was used for next step without further purification (580 mg, 70.4%).
Workup
- temperatureat reflux overnight
- customthe solvent was evaporated
- additionThe mixture was diluted with EtOAc (150 mL)
- washwashed with water, sat. Na2CO3aq
- dry with material, brine, and dried over MgSO4
- customThe solvent was evaporated
Sources & evidence
- ORD record
- ord-8ff54b2571a54a0fbec704ab580d56dd
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07674797B2
Reaction notes
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