Ethyl Acetate → 4-(4-bromo-1H-imidazol-1-yl)-3-methoxybenzoic acid

HRID 71195Notes

Reaction equation

HRID 71195 reaction equation
F[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[CH:4][C:3]=1[O:12][CH3:13].[Br:14][C:15]1[N:16]=[CH:17][NH:18][CH:19]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C=O)C.O>[Br:14][C:15]1[N:16]=[CH:17][N:18]([C:2]2[CH:11]=[CH:10][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=2[O:12][CH3:13])[CH:19]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 592847Methyl 4-fluoro-3-methoxybenzoateHCID 178418934HCID 178418934, compound

Product 1

HCID 666082014-(4-bromo-1H-imidazol-1-yl)-3-methoxybenzoic acidYield 55.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of methyl 4-fluoro-3-methoxybenzoate (2.13 g), 4-bromo-1H-imidazole (3.74 g) and potassium carbonate (4.80 g) in DMF (20 mL) was stirred at 100° C. overnight, and allowed to cool to room temperature, and ethyl acetate and water were added. The aqueous layer was separated, and acidified with 6N hydrochloric acid (pH=3-4), and the resultant precipitate was collected by filtration to give the title compound (1.92 g).

Workup

  1. temperatureto cool to room temperature
  2. customThe aqueous layer was separated
  3. filtrationthe resultant precipitate was collected by filtration

Sources & evidence

ORD record
ord-8c970c055dde43c78692552106cd5af1
Source dataset
uspto-grants-2014_09
Patent number
US08822699B2

Reaction notes

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