Methyl iodide → 4-Methoxydibenzothiophene

HRID 15240Notes

Reaction equation

HRID 15240 reaction equation
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[S:6][C:5]=2[C:4]([OH:14])=[CH:3][CH:2]=1.[C:15](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O.ClCCl>[CH3:15][O:14][C:4]1[C:5]2[S:6][C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=3[C:9]=2[CH:1]=[CH:2][CH:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 1548734-Hydroxydibenzothiophene

Product 1

HCID 4583544-Methoxydibenzothiophene

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of dibenzothiophen-4-ol (i)(14.2 g, 71.0 mmol) in acetone (500 ml) was added powdered potassium carbonate (14.72 g, 106.5 mmol) and methyl iodide (4.43 ml, 71 mmol). The mixture was heated to reflux and stirred like this for 16 hours. The mixture was then cooled and filtered through a Celite™ pad. The resulting filtrant was concentrated in vacuo to give an oily residue that was diluted in dichloromethane (100 ml) and washed with 1M NaOH and saturated brine solution. The organic layer was dried using MgSO4, filtered and concentrated in vacuo to give a buff coloured solid that corresponded to the title compound and was used without any further purification. (15.2 g, 100%) m/z (LC-MS, ESP), RT=4.22 min, (M+H)=215.1

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. temperatureThe mixture was then cooled
  4. filtrationfiltered through a Celite™ pad
  5. concentrationThe resulting filtrant was concentrated in vacuo
  6. customto give an oily residue that
  7. washwashed with 1M NaOH and saturated brine solution
  8. customThe organic layer was dried
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customto give a buff

Sources & evidence

ORD record
ord-c786ad1ddf13477fa9e58cb47e544877
Source dataset
uspto-grants-2010_06
Patent number
US07732483B2

Reaction notes

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