N-bromobutanimide → 4-Bromo-2-(4-fluoro-phenyl)-5-[2-(4-fluoro-phenyl)-ethyl]-1-methyl-1,2-dihydro-pyrazol-3-one

HRID 1993925Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1993925
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[CH:11]=[C:10]([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[N:9]2[CH3:23])=[CH:4][CH:3]=1.[Br:24]N1C(=O)CCC1=O>C(Cl)Cl.[Al]>[Br:24][C:11]1[C:12](=[O:13])[N:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[N:9]([CH3:23])[C:10]=1[CH2:14][CH2:15][C:16]1[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=1

Komponenten

5

Edukt 2

HCID 67184N-bromobutanimideHCID 686794792-(4-Fluoro-phenyl)-5-[2-(4-fluoro-phenyl)-ethyl]-1-methyl-1,2-dihydro-pyrazol-3-one

Produkt 1

HCID 686775324-Bromo-2-(4-fluoro-phenyl)-5-[2-(4-fluoro-phenyl)-ethyl]-1-methyl-1,2-dihydro-pyrazol-3-oneAusbeute 84,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 5359268AluminumLösungsmittel

Versuchsvorschrift

To a solution of 2-(4-fluoro-phenyl)-5-[2-(4-fluoro-phenyl)-ethyl]-1-methyl-1,2-dihydro-pyrazol-3-one (0.296 g) in methylene chloride (5 mL) was added N-bromosuccinimide (0.168 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-2-(4-fluoro-phenyl)-5-[2-(4-fluoro-phenyl)-ethyl]-1-methyl-1,2-dihydro-pyrazol-3-one (0.312 g) as a white solid. MS (ESI+): 395.0 ([M+H]+).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-b8c87bb180444f4490d452bd68659b72
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07652057B2

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