Methyl iodide → 3-Bromothioanisole

HRID 22592

Reaction equation

HRID 22592 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([SH:8])[CH:5]=[CH:6][CH:7]=1.[C:9](=O)([O-])[O-].[K+].[K+].IC>CC(C)=O>[CH3:9][S:8][C:4]1[CH:3]=[C:2]([Br:1])[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 80597m-Bromobenzenethiol

Product 1

HCID 27356273-Bromothioanisole

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 3-bromothiophenol (10 g) in acetone (250 mL) was added potassium carbonate (14.6 g) and iodomethane (4.28 mL). The heterogenous mixture was refluxed for 4 hrs., cooled to room temperature, filtered, and concentrated under reduced pressure. Ether (200 mL) was added, and the mixture was filtered again and finally evaporated to dryness to yield the title compound.

Workup

  1. temperatureThe heterogenous mixture was refluxed for 4 hrs
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure
  4. additionEther (200 mL) was added
  5. filtrationthe mixture was filtered again
  6. customfinally evaporated to dryness

Sources & evidence

ORD record
ord-581984c1318441db9e89fd4f881319b7
Source dataset
uspto-grants-1995_06
Patent number
US05428171

Linked notes

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