Potassium Hydroxide → 3-(1H-imidazol-2-ylmethoxy)-4-iodobenzaldehyde

HRID 2035688Notes

Reaction equation

HRID 2035688 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[I:10])[CH:5]=[O:6].[OH-].[K+].Cl.Cl[CH2:15][C:16]1[NH:17][CH:18]=[CH:19][N:20]=1>CS(C)=O.C(Cl)Cl.O>[NH:17]1[CH:18]=[CH:19][N:20]=[C:16]1[CH2:15][O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[I:10])[CH:5]=[O:6]

Participants

7

Reactant 3

HCID 14797Potassium HydroxideHCID 27609292-(Chloromethyl)-1H-imidazole hydrochlorideHCID 27752703-Hydroxy-4-iodobenzaldehyde

Product 1

HCID 866614633-(1H-imidazol-2-ylmethoxy)-4-iodobenzaldehydeYield 43.1%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a flask, were added 3-hydroxy-4-iodobenzaldehyde (200 mg, 0.806 mmol), KOH (43.0 mg, 0.766 mmol) and DMSO (2 ml). The mixture was stirred at rt for 2 h. 2-(chloromethyl)-1H-imidazole hydrochloride (105.4 mg, 0.689 mmol) in 1 ml of DMSO was added to this mixture and stirred overnight. The mixture was diluted with DCM and water. The organic phase was washed with brine, dried over sodium sulfate and concentrated to afford crude product, which was purified on silica gel (MeOH/DCM=8/92) to afford desire product (97.4 mg, 0.297 mmol, 36.8% yield).

Workup

  1. stirringstirred overnight
  2. washThe organic phase was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customto afford crude product, which
  6. customwas purified on silica gel (MeOH/DCM=8/92)

Sources & evidence

ORD record
ord-abdf1c531b1144b7b183e425adcf6634
Source dataset
uspto-grants-2013_11
Patent number
US08575150B2

Reaction notes

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