Acetylacetone → 5-bromo-2-(3,5-dimethyl-1H-pyrazol-1-yl)phenol

HRID 337355Notes

Reaction equation

HRID 337355 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:9][NH2:10])=[C:6]([OH:8])[CH:7]=1.C[C:12]1[CH:17]=[CH:16]C(S([O-])(=O)=O)=[CH:14][CH:13]=1.C(CC(=O)C)(=O)C>C(O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:9]2[C:17]([CH3:16])=[CH:12][C:13]([CH3:14])=[N:10]2)=[C:6]([OH:8])[CH:7]=1

Participants

4

Reactant 2

HCID 31261AcetylacetoneHCID 1317320185-Bromo-2-hydrazinylphenol;4-methylbenzenesulfonate

Product 1

HCID 601440505-bromo-2-(3,5-dimethyl-1H-pyrazol-1-yl)phenolYield 101.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-bromo-2-hydrazinylphenol 4-methylbenzenesulfonate (0.9 g) and acetylacetone (0.8 g) were added to ethanol (25 mL) refluxed for 1 h. Then the reaction mixture was cooled to room temperature and the solvent was evaporated under reduced pressure. The residue was dissolved in ethyl acetate (50 mL) and washed with saturated sodium bicarbonate solution (20 mL×2). The organic layer was dried over anhydrous Na2SO4, and concentrated under reduced pressure. The resulting residue was chromatographed over silica gel column eluted with hexane/ethyl acetate (4:1) to yield the title compound (650 mg).

Workup

  1. temperaturerefluxed for 1 h
  2. customthe solvent was evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate (50 mL)
  4. washwashed with saturated sodium bicarbonate solution (20 mL×2)
  5. dry with materialThe organic layer was dried over anhydrous Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was chromatographed over silica gel column
  8. washeluted with hexane/ethyl acetate (4:1)

Sources & evidence

ORD record
ord-1d041e77e4bc4bbc9c1e349d38beb363
Source dataset
uspto-grants-2014_11
Patent number
US08889727B2

Reaction notes

Loading…