4-Chlorophenol → HCID 16063515, compound

HRID 1993928Notes

Reaction equation

HRID 1993928 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.Br[CH2:12][C:13]1[N:17]([CH3:18])[N:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:15](=[O:25])[C:14]=1[CH:26]([CH3:28])[CH3:27]>CN(C=O)C.O.CCOC(C)=O>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:12][C:13]2[N:17]([CH3:18])[N:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:15](=[O:25])[C:14]=2[CH:26]([CH3:28])[CH3:27])=[CH:6][CH:5]=1

Participants

7

Reactant 3

HCID 46844-ChlorophenolHCID 24758Sodium hydrideHCID 12883634HCID 12883634, compound

Product 1

HCID 16063515HCID 16063515, compoundYield 17.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of sodium hydride (0.023 g of a 50% dispersion in mineral oil) in DMF (2 mL) at 0° C. was added 4-chlorophenol (0.042 g). To this was added a solution of 5-bromomethyl-4-isopropyl-1-methyl-2-phenyl-1,2-dihydro-pyrazol-3-one (0.10 g) in DMF (1 mL) and the reaction mixture was allowed to stir at ambient temperature for 18 hours. The reaction was then diluted with water and EtOAc. The phases were separated and the aqueous was extracted with further EtOAc. The combined organic phases were washed with further brine and dried with sodium sulfate. Filtration and evaporation of the volatiles in vacuo and purification of the residue via ISCO Combiflash chromatography (using EtOAc/heptane) afforded the 5-(4-chloro-phenoxymethyl)-4-isopropyl-1-methyl-2-phenyl-1,2-dihydro-pyrazol-3-one (0.020 g) as a light yellow solid. MS (ESI+): 357.1 [M+H]+).

Workup

  1. customThe phases were separated
  2. extractionthe aqueous was extracted with further EtOAc
  3. washThe combined organic phases were washed with further brine
  4. dry with materialdried with sodium sulfate
  5. filtrationFiltration and evaporation of the volatiles
  6. customin vacuo and purification of the residue via ISCO Combiflash chromatography (using EtOAc/heptane)

Sources & evidence

ORD record
ord-a569a7feda4c498888bc35dfca4a2c46
Source dataset
uspto-grants-2010_01
Patent number
US07652057B2

Reaction notes

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