Bromine → HCID 68677142, compound

HRID 1993918Notes

Reaction equation

HRID 1993918 reaction equation
[CH:1]1([C:4]2[C:5](=[O:17])[N:6]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:7]([CH3:10])[C:8]=2[CH3:9])[CH2:3][CH2:2]1.[Br:18]Br>O1CCOCC1.O.CCOC(C)=O>[Br:18][CH2:9][C:8]1[N:7]([CH3:10])[N:6]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:5](=[O:17])[C:4]=1[CH:1]1[CH2:3][CH2:2]1

Participants

6

Reactant 2

HCID 24408BromineHCID 68676759HCID 68676759, compound

Product 1

HCID 68677142HCID 68677142, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To 4-cyclopropyl-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one (0.081 g) in a round bottom flask under argon in dioxane (1.5 mL) was added bromine (0.057 g). The reaction was stirred at ambient temperature for 2 days. The reaction was diluted with water and EtOAc and the phases were separated. The aqueous phase was extracted with more EtOAc and the combined organic phases were washed with brine, dried over sodium sulfate, filtered and evaporated in vacuo. The crude material was purified via ISCO combiflash chromatography (EtOAc/heptane) to afford the desired 5-Bromomethyl-4-cyclopropyl-1-methyl-2-phenyl-1,2-dihydro-pyrazol-3-one as a light brown solid. MS (ESI+): 307.1 ([M+H]+).

Workup

  1. customthe phases were separated
  2. extractionThe aqueous phase was extracted with more EtOAc
  3. washthe combined organic phases were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe crude material was purified via ISCO combiflash chromatography (EtOAc/heptane)

Sources & evidence

ORD record
ord-184612df7eda4c0ea994051861f14539
Source dataset
uspto-grants-2010_01
Patent number
US07652057B2

Reaction notes

Loading…