Bromine → HCID 178437570, compound

HRID 2356703Notes

Reaction equation

HRID 2356703 reaction equation
[CH2:1]([C:3]1[N:4]=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)[NH:6][CH:7]=1)[CH3:2].[Br:15]Br.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[Br:15][C:7]1[NH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)=[N:4][C:3]=1[CH2:1][CH3:2]

Participants

5

Reactant 3

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 178437178HCID 178437178, compound

Product 1

HCID 178437570HCID 178437570, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a suspension of 4-ethyl-2-(4-fluorophenyl)imidazole (4.90 g) in chloroform (100 ml) was added bromine (4.53 g), and the mixture was stirred at room temperature for 3 hours. To the reaction mixture was added a saturated aqueous sodium hydrogen carbonate solution, and the organic layer was collected. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The resulting residue was crystallized from chloroform to obtain 5-bromo-4-ethyl-2-(4-fluorophenyl)-imidazole (5.16 g) as colorless crystal. 53 mg of the product was treated with 4N hydrogen chloride-dioxane solution to obtain 5-bromo-4-ethyl-2-(4-fluorophenyl)imidazole (60 mg) as colorless crystal.

Workup

  1. customthe organic layer was collected
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe resulting residue was crystallized from chloroform

Sources & evidence

ORD record
ord-cea69ca300a442c09824ae74a629db5b
Source dataset
uspto-grants-2010_07
Patent number
US07759373B2

Reaction notes

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