Methyl iodide → 1-Iodo-3-(methoxymethyl)benzene

HRID 1594000Notes

Reaction equation

HRID 1594000 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6].IC.[C:12](=O)([O-])[O-].[K+].[K+].[H-].[Na+]>CC#N.O>[CH3:12][O:6][CH2:5][C:4]1[CH:3]=[C:2]([I:1])[CH:9]=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 423003-Iodobenzyl alcohol

Product 1

HCID 229287461-Iodo-3-(methoxymethyl)benzeneYield 87.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
30 °C

Procedure

To a solution of 508 μl (4.0 mmol) of 3-iodobenzylalcohol and 1.25 ml (20.0 mmol) of iodomethane in MeCN (20 ml) there were added 829 mg (6.0 mmol) of potassium carbonate. After stirring 3 h at 30° C., 320 mg (8.00 mmol) of NaH were added and stirring was continued a further 3 h at RT. Water was then added to the reaction mixture, which was extracted with chloroform. The organic phase was successively washed with water and a satd aq. NaCl soln and dried over MgSO4. Following filtration and removal of the solvent in vacuo there were obtained 863 mg (3.5 mmol, 87%) of 3-methoxymethyliodobenzene.

Workup

  1. stirringstirring
  2. waitwas continued a further 3 h at RT
  3. extractionwas extracted with chloroform
  4. washThe organic phase was successively washed with water
  5. dry with materiala satd aq. NaCl soln and dried over MgSO4
  6. filtrationfiltration and removal of the solvent in vacuo

Sources & evidence

ORD record
ord-c6a5520588f74ce688898db1a417d5d3
Source dataset
uspto-grants-2007_11
Patent number
US07300939B2

Reaction notes

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