Aniline → 3-Bromo-1-phenylpyrrolidin-2-one

HRID 1951746Notes

Reaction equation

HRID 1951746 reaction equation
[C:1]1([NH2:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[Br:16][CH:17]([CH2:21][CH2:22]Br)[C:18](Cl)=[O:19].[OH-].[Na+]>C(#N)C>[Br:16][CH:17]1[CH2:21][CH2:22][N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:18]1=[O:19]

Participants

6

Reactant 4

HCID 6115AnilineHCID 14798Sodium HydroxideHCID 62657Potassium Phosphate, TribasicHCID 44131432,4-Dibromobutyryl chloride

Product 1

HCID 34652323-Bromo-1-phenylpyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of phenylamine L (465 mg, 5.0 mmol) and potassium phosphate (530 mg, 2.5 mmol) in acetonitrile (20 mL) was added 2,4-dibromo-butyryl chloride III (1.32 g, 5.0 mmol) at 0° C. The mixture was brought to rt and stirred for 1 hr. Then NaOH (1 mL, 50% aqueous solution) was added, and the mixture was stirred overnight. After the mixture was filtered, the solid was washed with acetonitrile (10 mL), and the combined filtrate was concentrated. The residue was purified by column chromatography (eluate: EtOAc/petroleum ether from 1/5 to 1/3) to afford 3-bromo-1-phenyl-pyrrolidin-2-one LI as white solid.

Workup

  1. customwas brought to rt
  2. stirringthe mixture was stirred overnight
  3. filtrationAfter the mixture was filtered
  4. washthe solid was washed with acetonitrile (10 mL)
  5. concentrationthe combined filtrate was concentrated
  6. customThe residue was purified by column chromatography (eluate: EtOAc/petroleum ether from 1/5 to 1/3)

Sources & evidence

ORD record
ord-b6de255e061d47b19a6db3c0a93ab4ed
Source dataset
uspto-grants-2013_03
Patent number
US08404738B2

Reaction notes

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