Imidazole → HCID 728760, compound

HRID 217873Notes

Reaction equation

HRID 217873 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.C(O[K])(C)(C)C.F[C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:14]=1[N+:23]([O-:25])=[O:24].CCOC(C)=O>CS(C)=O>[N+:23]([C:14]1[CH:15]=[C:16]([C:19]([F:20])([F:21])[F:22])[CH:17]=[CH:18][C:13]=1[N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1)([O-:25])=[O:24]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 8857Ethyl AcetateHCID 677784-Fluoro-3-nitrobenzotrifluorideHCID 178418922HCID 178418922, compound

Product 1

HCID 728760HCID 728760, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of imidazole (0.997 g, 14.65 mmol) and tert-BuOK (1.722 g, 15.35 mmol) was put under Ar in a 100 mL and dissolved in dry DMSO (15 mL) to give a colorless solution. After 5 min, 1-fluoro-2-nitro-4-(trifluoromethyl)benzene (2.04 mL, 14.58 mmol) was added within 30 s, immediately leading to a darkening of the rm to black. A temperature rise was also noted. The black solution was stirred at RT for 20 min. Ice water (60 mL) and EtOAc (50 mL) were added, the organic layer was isolated, and the aqueous phase was extracted twice with 20 mL EtOAc. The organic layer was washed with H2O (2×30 mL), brine, dried, filtered and evaporated to give the title compound as an orange oil. Yield: 3.66 g (97%).

Workup

  1. customto give a colorless solution
  2. customthe organic layer was isolated
  3. extractionthe aqueous phase was extracted twice with 20 mL EtOAc
  4. washThe organic layer was washed with H2O (2×30 mL), brine
  5. customdried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-2fb8cc383a334ea999fef4e45457ce48
Source dataset
uspto-grants-2012_06
Patent number
US08198279B2

Reaction notes

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