Water → 3,5-Dimethylthioanisole

HRID 498138Notes

Reaction equation

HRID 498138 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([SH:9])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[C:10](=O)([O-])[O-].[K+].[K+].IC.O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CS(C)=O>[CH3:8][C:6]1[CH:5]=[C:4]([S:9][CH3:10])[CH:3]=[C:2]([CH3:1])[CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 1175483,5-Dimethylbenzenethiol

Product 1

HCID 27586623,5-DimethylthioanisoleYield 88%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

10.0 g (0.072 mol) of 3,5-dimethylbenzenethiol, 9.95 g (0.072 mol) of potassium carbonate and 0.46 g (1.4 mmol) of tetrabutylammonium bromide are suspended in 20 ml of dimethylsulfoxide under argon. Iodomethane (10.2 g, 0.072 mol) is added dropwise, and the mixture is stirred 16 h at ambient temperature. After pouring the mixture into water, the product is extracted with ether, washed with water, dried over sodium sulfate and concentrated in vacuo. The crude product 9.6 g (0.063 mol; 88%) is obtained as a slightly yellow oil, and is used for the next step without further purification.

Workup

  1. extractionthe product is extracted with ether
  2. washwashed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9b7954d005c44c1fae953012240b3f0d
Source dataset
uspto-grants-2005_09
Patent number
US06949678B2

Reaction notes

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