Imidazole → 1-(3-bromophenyl)-1H-imidazole

HRID 902570Notes

Reaction equation

HRID 902570 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6](F)[CH:7]=[CH:8][CH:9]=1.[NH:11]1[CH:15]=[CH:14][N:13]=[CH:12]1>CS(C)=O.C(OCC)(=O)C>[Br:3][C:4]1[CH:5]=[C:6]([N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 140821-Bromo-3-fluorobenzeneHCID 24758Sodium hydride

Product 1

HCID 3120961-(3-bromophenyl)-1H-imidazole

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

In an amount of 400 mg of imidazole was dissolved in 7.5 ml of dimethyl sulfoxide under argon atmosphere, added with 255 mg of 60% sodium hydride, and stirred at room temperature. After 1 hour, the reaction mixture was added with 0.8 ml of 3-bromofluorobenzene, and stirred at 140° C. for 21 hours. The reaction mixture was diluted with 50 ml of ethyl acetate, and washed with 20 ml of saturated brine. The organic layer was dried over anhydrous sodium sulfate, and then filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate (3:1 to 1:1)) to obtain 1.1 g of the title compound.

Workup

  1. stirringstirred at 140° C. for 21 hours
  2. washwashed with 20 ml of saturated brine
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate (3:1 to 1:1))

Sources & evidence

ORD record
ord-d96ec62d39884e1a8e98cb901f9fad77
Source dataset
uspto-grants-2008_04
Patent number
US07365174B2

Reaction notes

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