Potassium Carbonate → 1-(5-Fluoro-2-nitrophenyl)-4-methyl-1H-imidazole

HRID 254290Notes

Reaction equation

HRID 254290 reaction equation
F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH3:12][C:13]1[N:14]=[CH:15][NH:16][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[F:8][C:6]1[CH:5]=[CH:4][C:3]([N+:9]([O-:11])=[O:10])=[C:2]([N:16]2[CH:17]=[C:13]([CH3:12])[N:14]=[CH:15]2)[CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 679672,4-DifluoronitrobenzeneHCID 178418800HCID 178418800, compound

Product 1

HCID 577324471-(5-Fluoro-2-nitrophenyl)-4-methyl-1H-imidazoleYield 50.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2,4-difluoro-1-nitrobenzene (50 g, 314 mmol), 4-methyl-1H-imidazole (25.7 g, 314 mmol) and potassium carbonate (100 g, 725 mmol) in dichloromethane (600 mL) was stirred at room temperature for 4 days. The mixture was washed with water then dried over magnesium sulfate. Solvent was removed under reduced pressure and the residue was recrystallized in ethyl acetate to provide product 1A as a yellow solid (35 g, 50% yield). EIMS 221.9 [M+H]+.

Workup

  1. washThe mixture was washed with water
  2. dry with materialthen dried over magnesium sulfate
  3. customSolvent was removed under reduced pressure
  4. customthe residue was recrystallized in ethyl acetate

Sources & evidence

ORD record
ord-6b8524042a384a97a2e4fd1af46355be
Source dataset
uspto-grants-2011_01
Patent number
US07875618B2

Reaction notes

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