Bromine → 4-bromo-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazole-5-carbaldehyde

HRID 1661945Notes

Reaction equation

HRID 1661945 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:14]([CH2:15][CH2:16][O:17][CH3:18])[C:13]3[C:19]([O:25][CH3:26])=[CH:20][C:21]([CH:23]=[O:24])=[CH:22][C:12]=3[N:11]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[Br:27]Br>C(O)(=O)C>[Br:27][C:22]1[C:12]2[N:11]=[C:10]([C:7]3[CH:8]=[CH:9][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:5][CH:6]=3)[N:14]([CH2:15][CH2:16][O:17][CH3:18])[C:13]=2[C:19]([O:25][CH3:26])=[CH:20][C:21]=1[CH:23]=[O:24]

Participants

4

Reactant 2

HCID 24408BromineHCID 577720462-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazole-5-carbaldehyde

Product 1

HCID 577720644-bromo-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazole-5-carbaldehyde

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3.0 g (8.51 mmol) of 2-(4-Isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazole-5-carbaldehyde is dissolved in 90 ml acetic acid. Bromine (437 ul, 8.51 mmol) is added dropwise and the reaction is stirred for 5 h at RT. Ice/water is added and the reaction mixture is extracted with ethyl acetate (3×). The organic layer is washed with water (3×) and brine (2×), dried (Na2SO4) and concentrated in vacuo. The residue is purified by flash-chromatography on silica gel (hexanes/EtOAc) to give 2:08 g of colorless crystals.

Workup

  1. extractionthe reaction mixture is extracted with ethyl acetate (3×)
  2. washThe organic layer is washed with water (3×) and brine (2×)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by flash-chromatography on silica gel (hexanes/EtOAc)
  6. customto give 2:08 g of colorless crystals

Sources & evidence

ORD record
ord-9da75cba45f94fc5ab83fa660d00837c
Source dataset
uspto-grants-2011_10
Patent number
US08030497B2

Reaction notes

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