Imidazole → Benzonitrile, 2-fluoro-4-(1H-imidazol-1-ylmethyl)-

HRID 1594844Notes

Reaction equation

HRID 1594844 reaction equation
Br[CH2:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[C:5]([F:11])[CH:4]=1.[NH:12]1[CH:16]=[CH:15][N:14]=[CH:13]1>CN(C=O)C>[F:11][C:5]1[CH:4]=[C:3]([CH2:2][N:12]2[CH:16]=[CH:15][N:14]=[CH:13]2)[CH:10]=[CH:9][C:6]=1[C:7]#[N:8]

Participants

4

Reactant 2

HCID 795ImidazoleHCID 27784664-Cyano-3-fluorobenzyl bromide

Product 1

HCID 21697068Benzonitrile, 2-fluoro-4-(1H-imidazol-1-ylmethyl)-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Bromomethyl-2-fluoro-benzonitrile, as described in Step D above, (3.44 g, 16.0 mmol) and imidazole (5.47 g, 80.3 mmol) were dissolved in DMF (40 mL) and stirred at ambient temperature for 2 h. The DMF was removed in vacuo and the residue was partitioned between EtOAc (300 mL) and aqueous saturated NaHCO3 solution. The organic layer was separated, washed with NaHCO3 solution, H2O, brine, and dried (MgSO4). Filtration and concentration to dryness gave the title compound after chromatography (silica gel, 1-2% CH3OH/CH2Cl2).

Workup

  1. customThe DMF was removed in vacuo
  2. customthe residue was partitioned between EtOAc (300 mL) and aqueous saturated NaHCO3 solution
  3. customThe organic layer was separated
  4. washwashed with NaHCO3 solution, H2O, brine
  5. dry with materialdried (MgSO4)
  6. filtrationFiltration and concentration to dryness

Sources & evidence

ORD record
ord-d4ccc69029704860bc8b63a1c5f4259a
Source dataset
uspto-grants-2001_09
Patent number
US06284755B1

Reaction notes

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