Ethyl Acetate → HCID 57772088, compound

HRID 1661907Notes

Reaction equation

HRID 1661907 reaction equation
[I:1][C:2]1[CH:19]=[C:18]([O:20][CH3:21])[C:5]2[NH:6][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:22]Br.CCOC(C)=O>C(O)(=O)C>[Br:22][C:3]1[C:4]2[N:8]=[C:7]([C:9]3[CH:10]=[CH:11][C:12]([CH:15]([CH3:17])[CH3:16])=[CH:13][CH:14]=3)[NH:6][C:5]=2[C:18]([O:20][CH3:21])=[CH:19][C:2]=1[I:1]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 24408BromineHCID 178492957HCID 178492957, compound

Product 1

HCID 57772088HCID 57772088, compoundYield 52.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 200 mg (0.51 mmol) 5-iodo-2-(4-isopropyl-phenyl)-7-methoxy-1H-benzoimidazole in 3 ml glacial acetic acid is slowly added 82 mg (0.51 mmol) bromine. The reaction mixture is stirred for 45 min. 30 ml EtOAc are added and this solution is washed 2n NaOH, water and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue is purified by flash-chromatography on silica gel (hexane:EtOAc=3:1) and recrystallized from EtOAc/diethyl ether to afford 126 mg of the title compound as off-white crystals.

Workup

  1. washthis solution is washed 2n NaOH, water and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by flash-chromatography on silica gel (hexane:EtOAc=3:1)
  6. customrecrystallized from EtOAc/diethyl ether

Sources & evidence

ORD record
ord-f305f1f02bde488fa16e74e652f8ec81
Source dataset
uspto-grants-2011_10
Patent number
US08030497B2

Reaction notes

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