N-bromobutanimide → HCID 68676898, compound

HRID 1993914Notes

Reaction equation

HRID 1993914 reaction equation
[CH:1]1([C:4]2[N:8]([CH3:9])[N:7]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:6](=[O:16])[CH:5]=2)[CH2:3][CH2:2]1.[Br:17]N1C(=O)CCC1=O>C(Cl)Cl.[Al]>[Br:17][C:5]1[C:6](=[O:16])[N:7]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:8]([CH3:9])[C:4]=1[CH:1]1[CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 68678873HCID 68678873, compound

Product 1

HCID 68676898HCID 68676898, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 5359268AluminumSolvent

Procedure

To a solution of 5-cyclopropyl-1-methyl-2-phenyl-1,2-dihydro-pyrazol-3-one (3.35 g) in methylene chloride (80 mL) was added N-bromosuccinimide (2.78 g). The reaction vessel was wrapped in aluminium foil and stirred for 24 hours. The solvent was evaporated in vacuo and the residue was dissolved in EtOAc and water. The phases were separated and the aqueous phase was extracted with more EtOAc. The combined organic phases were washed with brine, dried over sodium sulfate, filtered and reduced in vacuo to give a crude residue. Flash column chromatography over silica gel using ISCO combiflash chromatography and eluting with EtOAc/heptane afforded the desired 4-bromo-5-cyclopropyl-1-methyl-2-phenyl-1,2-dihydro-pyrazol-3-one (3.89 g) as a light brown solid. MS (ESI+): 293.1 ([M+H]+).

Workup

  1. customThe solvent was evaporated in vacuo
  2. dissolutionthe residue was dissolved in EtOAc
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted with more EtOAc
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customto give a crude residue
  9. washFlash column chromatography over silica gel using ISCO combiflash chromatography and eluting with EtOAc/heptane

Sources & evidence

ORD record
ord-bfa105cf65024998a0ac6ce759d77c31
Source dataset
uspto-grants-2010_01
Patent number
US07652057B2

Reaction notes

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