Dimethyl Disulfide → 3-Methyl-4-(methylthio)anisole

HRID 1892062Notes

Reaction equation

HRID 1892062 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH3:10].C([Li])CCC.[CH3:16][S:17]SC>C1COCC1>[CH3:10][C:3]1[CH:4]=[C:5]([O:8][CH3:9])[CH:6]=[CH:7][C:2]=1[S:17][CH3:16]

Participants

5

Reactant 3

HCID 12232Dimethyl DisulfideHCID 1179151-Bromo-4-methoxy-2-methylbenzeneHCID 178418339Butyllithium

Product 1

HCID 5978063-Methyl-4-(methylthio)anisoleYield 96.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the cold (−78° C.) solution of 2-bromo-5-methoxy toluene (8 g, 0.04 mol) in dry THF (80 mL) under inert atmosphere, butyl lithium solution (1.6M solution in hexane; 36.8 mL, 0.058 mol) was added dropwise and the mixture was stirred for 1 h at same temperature. Dimethyl disulphide (7.7 mL, 0.08 mol) was then added dropwise and the reaction mixture was allowed to warm to room temperature over a period of 2 h. The reaction mixture was quenched with sat. ammonium chloride solution and extracted in diethyl ether. The combined organic extracts were washed with water and brine and dried. The solvent was evaporated in vacuo to yield 6.5 g of 2-methyl-4-methoxy thioanisole, which was used as such in Step 2 MS m/z 168 (M+).

Workup

  1. customThe reaction mixture was quenched with sat. ammonium chloride solution
  2. extractionextracted in diethyl ether
  3. washThe combined organic extracts were washed with water and brine
  4. customdried
  5. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-fc5ab9c5daf240d9af6187c79c670ea8
Source dataset
uspto-grants-2013_08
Patent number
US08507509B2

Reaction notes

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