Methyl iodide → HCID 67184879, compound

HRID 1843676Notes

Reaction equation

HRID 1843676 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][NH:5][C:6]=1[C:7]1[C:12]([F:13])=[CH:11][CH:10]=[C:9]([N+:14]([O-:16])=[O:15])[C:8]=1[F:17].[CH3:18]I>ClCCl.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.[OH-].[Na+]>[Br:1][C:2]1[C:6]([C:7]2[C:12]([F:13])=[CH:11][CH:10]=[C:9]([N+:14]([O-:16])=[O:15])[C:8]=2[F:17])=[N:5][N:4]([CH3:18])[CH:3]=1

Participants

6

Reactant 2

HCID 6328Methyl iodideHCID 67184739HCID 67184739, compound

Product 1

HCID 67184879HCID 67184879, compoundYield 57.5%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a mixture of 4-bromo-5-(2,6-difluoro-3-nitrophenyl)-1H-pyrazole (0.88 g, 2.9 mmol) and methyl iodide (2 mL, 32 mmol) in dichloromethane (20 mL), tetrabutylammonium bromide (0.32 g, 1 mmol) in 7 N sodium hydroxide (20 mL) was added and the mixture was rapidly stirred at room temperature for 3 h. The phases were separated and the organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated. The crude residue was purified by flash chromatography (eluant: dichloromethane/petroleum ether 2:1). The title compound, mixture of the two regioisomers, was obtained as a waxy solid (0.53 g, 57%).

Workup

  1. additionwas added
  2. customThe phases were separated
  3. washthe organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe crude residue was purified by flash chromatography (eluant: dichloromethane/petroleum ether 2:1)
  7. additionThe title compound, mixture of the two regioisomers

Sources & evidence

ORD record
ord-5016e47df0ac435e8b20cc5c3fd368a2
Source dataset
uspto-grants-2015_02
Patent number
US08946250B2

Reaction notes

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