Reaction #1755456

ord-0cef180ce2cc4b3cbe4fcec96a5d2fd5

Reaction equation

c1c[nH]cn1
imidazole
COC(=O)c1ccc(F)cc1
methyl 4-fluorobenzoate
O=C([O-])[O-].[K+].[K+]
potassium carbonate
→
COC(=O)c1ccc(-n2ccnc2)cc1
1-(4′-methoxycarbonylphenyl)imidazole
Yield 59.0%

Reactants

—
ice water
c1c[nH]cn1
imidazole
COC(=O)c1ccc(F)cc1
methyl 4-fluorobenzoate
O=C([O-])[O-].[K+].[K+]
potassium carbonate

Reagents

None

Solvents

CS(C)=O
DMSO

Conditions

Temperature
120°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    TemperatureAfter cooling to room temperature
  2. 2
    FiltrationPrecipitated product is filtered off
  3. 3
    Washwashed with water

Procedure

A mixture of imidazole (132 g, 1.9 mol), methyl 4-fluorobenzoate (170 ml, 1.3 mol) and potassium carbonate (357 g, 2.6 mol) in DMSO (200 ml) is stirred at 120° C. for 3 h. After cooling to room temperature, the mixture is added to ice-water. Precipitated product is filtered off and washed with water. Yield: 59%.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07989091B2uspto-grants-2011_08