Ethyl Acetate → 5-benzyl-4-bromo-2-(4-isopropylphenyl)-7-methoxy-1-(2-methoxyethyl)-1H-benzo[d]imidazole

HRID 1661912Notes

Reaction equation

HRID 1661912 reaction equation
[Br:1]Br.[CH2:3]([C:10]1[CH:31]=[C:30]([O:32][CH3:33])[C:13]2[N:14]([CH2:26][CH2:27][O:28][CH3:29])[C:15]([C:17]3[CH:22]=[CH:21][C:20]([CH:23]([CH3:25])[CH3:24])=[CH:19][CH:18]=3)=[N:16][C:12]=2[CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CCOC(C)=O>C(O)(=O)C>[CH2:3]([C:10]1[CH:31]=[C:30]([O:32][CH3:33])[C:13]2[N:14]([CH2:26][CH2:27][O:28][CH3:29])[C:15]([C:17]3[CH:22]=[CH:21][C:20]([CH:23]([CH3:25])[CH3:24])=[CH:19][CH:18]=3)=[N:16][C:12]=2[C:11]=1[Br:1])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 24408BromineHCID 577720445-benzyl-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazole

Product 1

HCID 114887705-benzyl-4-bromo-2-(4-isopropylphenyl)-7-methoxy-1-(2-methoxyethyl)-1H-benzo[d]imidazoleYield 69.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

6 μl (0.122 mmol) bromine are added to a solution of 48 mg (0.116 mmol) 5-benzyl-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazole in 6 ml glacial acetic acid. The reaction mixture is stirred at room temperature for 10 min. 25 ml EtOAc are added and this solution is washed 4N NaOH (2×), water and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue is recrystallized from dichloromethane/diethyl ether/hexane to afford 40 mg of the title compound as colorless crystals.

Workup

  1. washthis solution is washed 4N NaOH (2×), water and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue is recrystallized from dichloromethane/diethyl ether/hexane

Sources & evidence

ORD record
ord-014db74243bc4a0a9b85bb823e02146f
Source dataset
uspto-grants-2011_10
Patent number
US08030497B2

Reaction notes

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