Water → 2-Bromo-1-(3-methoxy-2-nitro-phenyl)-4-methyl-1H-imidazole

HRID 254326Notes

Reaction equation

HRID 254326 reaction equation
[Br:1][C:2]1[NH:3][CH:4]=[C:5]([CH3:7])[N:6]=1.F[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[C:10]=1[N+:17]([O-:19])=[O:18].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[Br:1][C:2]1[N:3]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[C:10]=2[N+:17]([O-:19])=[O:18])[CH:4]=[C:5]([CH3:7])[N:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27827761-Fluoro-3-methoxy-2-nitrobenzeneHCID 178430836HCID 178430836, compound

Product 1

HCID 577324682-Bromo-1-(3-methoxy-2-nitro-phenyl)-4-methyl-1H-imidazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

2-bromo-4-methyl imidazole (3.7 g, 23.4 mmol) and 2-fluoro-6-methoxy-nitrobenzene were dissolved in DMF (80 mL). To this was then added potassium carbonate (6.3 g, 46.8 mmol). The reaction was heated to 90° C. for 16 hrs then poured into water and extracted with ethyl acetate. The organic layer was separated and washed with water then brined, dried over magnesium sulfate and filtered. The solvent was removed under reduced pressure and the crude purified by flash chromatography on silica gel in 20:1 ethyl acetate/methylene chloride. A tan solid (2.6 g) was recovered. MS (ES) m/z 311.9 [M+1]+

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent was removed under reduced pressure
  7. customthe crude purified by flash chromatography on silica gel in 20:1 ethyl acetate/methylene chloride
  8. customA tan solid (2.6 g) was recovered

Sources & evidence

ORD record
ord-21ff743ac3a846f49a199017ca34e9db
Source dataset
uspto-grants-2011_01
Patent number
US07875618B2

Reaction notes

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