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

HRID 1661905Notes

Reaction equation

HRID 1661905 reaction equation
[Br:1][C:2]1[CH:23]=[C:22]([O:24][CH3:25])[C:5]2[N:6]([CH2:18][CH2:19][O:20][CH3:21])[C:7]([C:9]3[CH:14]=[CH:13][C:12]([CH:15]([CH3:17])[CH3:16])=[CH:11][CH:10]=3)=[N:8][C:4]=2[CH:3]=1.[Br:26]Br.CCOC(C)=O>C(O)(=O)C>[Br:26][C:3]1[C:4]2[N:8]=[C:7]([C:9]3[CH:14]=[CH:13][C:12]([CH:15]([CH3:17])[CH3:16])=[CH:11][CH:10]=3)[N:6]([CH2:18][CH2:19][O:20][CH3:21])[C:5]=2[C:22]([O:24][CH3:25])=[CH:23][C:2]=1[Br:1]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 24408BromineHCID 113841195-Bromo-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazole

Product 1

HCID 111559124,5-dibromo-2-(4-isopropylphenyl)-7-methoxy-1-(2-methoxyethyl)-1H-benzo[d]imidazoleYield 6.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 403 mg (1.0 mmol) 5-bromo-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazole in 8 ml glacial acetic acid, 240 mg (1.5 mmol) bromine is slowly added at 10° C. The reaction mixture is allowed to warm to room temperature and is stirred for 3 h. 250 ml EtOAc are added and this solution is washed 1 n NaOH (2×), water and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue is recrystallized from EtOAc/hexane to afford 30 mg of the title compound as colorless crystals.

Workup

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

Sources & evidence

ORD record
ord-892cad9c80904e0589cafc8c8bc13bb8
Source dataset
uspto-grants-2011_10
Patent number
US08030497B2

Reaction notes

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