4-Iodophenol → Methyl 3-((4-iodophenoxy)methyl)benzoate

HRID 2112993Notes

Reaction equation

HRID 2112993 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=1)[C:12]([O:14][CH3:15])=[O:13].[I:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1>CC(C)=O>[CH3:15][O:14][C:12](=[O:13])[C:11]1[CH:16]=[CH:17][CH:18]=[C:9]([CH2:8][O:26][C:23]2[CH:24]=[CH:25][C:20]([I:19])=[CH:21][CH:22]=2)[CH:10]=1

Participants

5

Reactant 3

HCID 108944-IodophenolHCID 11430Potassium CarbonateHCID 517981Methyl 3-(bromomethyl)benzoate

Product 1

HCID 57643351Methyl 3-((4-iodophenoxy)methyl)benzoateYield 90.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Freshly ground potassium carbonate (8.3 g, 60 mmol) was added to a solution of methyl 3-bromomethyl-benzoate (12.83 g, 56 mmol; available from Lancaster Synthesis Ltd., Lancashire, UK) and 4-iodophenol (13.2 g, 60 mmol; available from Aldrich Chemical Company, Inc., Milwaukee, Wis.) in acetone (600 mL). The reaction mixture was heated at reflux overnight and then it was filtered and water was added. The resulting white solid was filtered off and dried in a vacuum oven overnight to give 3-(4-iodo-phenoxymethyl)-benzoic acid methyl ester (18.63 g, 90%) as a white solid

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. filtrationit was filtered
  4. additionwater was added
  5. filtrationThe resulting white solid was filtered off
  6. customdried in a vacuum oven overnight

Sources & evidence

ORD record
ord-60e9cfd57a2241eeb55c7cc0ef991c76
Source dataset
uspto-grants-2009_04
Patent number
US07524870B2

Reaction notes

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