Water → 1-(4-Bromophenyl)pyrrolidin-2-one

HRID 53504Notes

Reaction equation

HRID 53504 reaction equation
[C:1]1([N:7]2[CH2:11][CH2:10][CH2:9][C:8]2=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:13]Br.O.[OH-].[K+]>C(O)(=O)C>[Br:13][C:4]1[CH:3]=[CH:2][C:1]([N:7]2[CH2:11][CH2:10][CH2:9][C:8]2=[O:12])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 24408BromineHCID 783751-Phenylpyrrolidin-2-one

Product 1

HCID 7361101-(4-Bromophenyl)pyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

8.06 g of N-phenylpyrrolidinone were dissolved in 33 ml glacial acetic acid; the mixture was cooled to 0°-5° C. and then a solution of 2.65 ml bromine in 12 ml of glacial acetic acid was added dropwise. Stirring was continued for 30 minutes at room temperature. Work-up was accomplished by pouring the mixture into 1 l of water and neutralizing the mixture with KOH. The solid was filtered and dissolved in ethylacetate and washed with a sodium thiosulphate solution until the brown colour disappeared; washing with brine and drying with MgSO4 provided 8.5 g of a white crystalline mass that could be recrystallized from ether; m.p. 102° C.

Workup

  1. temperaturethe mixture was cooled to 0°-5° C.
  2. filtrationThe solid was filtered
  3. dissolutiondissolved in ethylacetate
  4. washwashed with a sodium thiosulphate solution until the brown colour
  5. washwashing with brine
  6. dry with materialdrying with MgSO4
  7. customprovided 8.5 g of a white crystalline mass that
  8. customcould be recrystallized from ether

Sources & evidence

ORD record
ord-036df159fdde45f8bcdaa037dc2e9a89
Source dataset
uspto-grants-1997_04
Patent number
US05620966

Reaction notes

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