Chloromethyl Methyl Ether → 1-Iodo-4-(methoxymethoxy)benzene

HRID 2080691Notes

Reaction equation

HRID 2080691 reaction equation
C(N(CC)C(C)C)(C)C.[CH3:10][O:11][CH2:12]Cl.[I:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1.[Cl-].[NH4+]>C(Cl)(Cl)Cl>[I:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:10][O:11][CH3:12])=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 108944-IodophenolHCID 25517Ammonium ChlorideHCID 81531Diisopropylethylamine

Product 1

HCID 110327301-Iodo-4-(methoxymethoxy)benzene

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2.33 ml of N,N-diisopropylethylamine and 900 μl of methoxymethyl chloride were added to a chloroform (20 ml) solution of 2 g of 4-iodophenol, and stirred overnight at room temperature. With cooling with ice, aqueous saturated ammonium chloride solution was added to it, extracted with ethyl acetate, and the organic layer was washed with saturated saline water. After dried, the solvent was evaporated away under reduced pressure, and the residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate) to obtain 1.08 g of the entitled compound as a colorless oil.

Workup

  1. additionwas added to it
  2. extractionextracted with ethyl acetate
  3. washthe organic layer was washed with saturated saline water
  4. customAfter dried
  5. customthe solvent was evaporated away under reduced pressure
  6. customthe residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-f324fe0581da4a6bbaeacc2cf7c16afb
Source dataset
uspto-grants-2011_04
Patent number
US07932394B2

Reaction notes

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