Imidazole → 1-(2-fluoro-4-nitrophenyl)-1H-imidazole

HRID 559005Notes

Reaction equation

HRID 559005 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1F.[NH:12]1[CH:16]=[CH:15][N:14]=[CH:13]1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1[N:12]1[CH:16]=[CH:15][N:14]=[CH:13]1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 11430Potassium CarbonateHCID 1230531,2-Difluoro-4-nitrobenzene

Product 1

HCID 53061531-(2-fluoro-4-nitrophenyl)-1H-imidazoleYield 96.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3,4-difluoronitrobenzene (1.00 mL, 9.03 mmol), imidazole (0.615 g, 9.04 mmol) and K2CO3 (2.50 g, 18.1 mmol) in DMF (10 mL) was stirred at room temperature overnight. Water (20 mL) was added to induce precipitation. The precipitate was collected, dried on vacuum to give 1-(2-fluoro-4-nitrophenyl)-1H-imidazole as a solid (1.81 g). MS 208.2 (M+H)

Workup

  1. customprecipitation
  2. customThe precipitate was collected
  3. customdried on vacuum

Sources & evidence

ORD record
ord-4b20f4cebb9d42299be69da5564c8cf7
Source dataset
uspto-grants-2011_11
Patent number
US08063058B2

Reaction notes

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