4,4-Dimethoxy-2-butanone → HCID 89649260, compound

HRID 2207637Notes

Reaction equation

HRID 2207637 reaction equation
[Cl-].[Br:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[F:11])[NH:6][NH3+:7].CO[CH:14](OC)[CH2:15][C:16](=O)[CH3:17]>C(O)C>[Br:2][C:3]1[CH:4]=[C:5]([N:6]2[CH:14]=[CH:15][C:16]([CH3:17])=[N:7]2)[CH:8]=[CH:9][C:10]=1[F:11]

Participants

4

Reactant 2

HCID 2285484,4-Dimethoxy-2-butanoneHCID 178479580HCID 178479580, compound

Product 1

HCID 89649260HCID 89649260, compoundYield 20.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (3-bromo-4-fluoro-anilino)ammonium chloride [CAS: 1166990-89-1](5412 mg, 22.41 mmol) in ethanol (30 mL) was added 4,4-dimethoxybutan-2-one (3.12 mL, 23.53 mmol), and the reaction was heated to reflux for 4 hours. The reaction mixture was concentrated in vacuo, and the residue was loaded onto silica (50 g, SNAP cartridge), eluting with EtOAc in isohexane from 0% to 25%. Fractions containing the faster running desired product were combined and concentrated in vacuo to give one of the isomers 1-(3-bromo-4-fluoro-phenyl)-3-methyl-pyrazole (D86) (1249 mg, 4.65 mmol, 20.8% yield) (1.26 g);

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 4 hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. washeluting with EtOAc in isohexane from 0% to 25%
  5. additionFractions containing the
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c66029ed0d904c2295bc991ac062b6d9
Source dataset
uspto-grants-2016_06
Patent number
US09376436B2

Reaction notes

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