Imidazole → 1-(2-Bromo-4-cyanophenyl)imidazole

HRID 1960001Notes

Reaction equation

HRID 1960001 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1F)[C:5]#[N:6].[NH:11]1[CH:15]=[CH:14][N:13]=[CH:12]1.[H-].[Na+].O>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([C:5]#[N:6])[CH:7]=[CH:8][C:9]=1[N:11]1[CH:15]=[CH:14][N:13]=[CH:12]1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 24758Sodium hydrideHCID 1235793-Bromo-4-fluorobenzonitrile

Product 1

HCID 688544441-(2-Bromo-4-cyanophenyl)imidazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

3-Bromo-4-fluorobenzonitrile (10.0 g, 50 mmol, 1 eq) and imidazole (5.1 g, 75 mmol, 1.5 eq) are dissolved in dimethylformamide (100 ml) and carefully admixed with sodium hydride (60% in mineral oil, 3.0 g, 75 mmol, 1.5 eq) under nitrogen at room temperature. The mixture is stirred at 100° C. for 4 hours. After cooling to room temperature, water (10 ml) is added and the mixture is evaporated to dryness. The residue is washed with water and petroleum ether and purified by column chromatography (silica gel, methyl tert-butyl ether/ethyl acetate gradient).

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe mixture is evaporated to dryness
  3. washThe residue is washed with water and petroleum ether
  4. custompurified by column chromatography (silica gel, methyl tert-butyl ether/ethyl acetate gradient)

Sources & evidence

ORD record
ord-41d967ea215b476da3c47dca8795b4d0
Source dataset
uspto-grants-2013_04
Patent number
US08410280B2

Reaction notes

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