Methyl iodide → 2-Trifluoromethylthioanisole

HRID 732763Notes

Reaction equation

HRID 732763 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[SH:9].[C:12](=O)([O-])[O-].[K+].[K+].IC>CN(C=O)C>[CH3:12][S:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[C:2]([F:1])([F:10])[F:11]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 27778892-(Trifluoromethyl)benzenethiol

Product 1

HCID 27607832-TrifluoromethylthioanisoleYield 88.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dissolve 2-trifluoromethyl-benzenethiol (10 g, 56 mmol), potassium carbonate (25 g, 180 mmol), iodomethane (11 mL, 177 mmol) in DMF (100 mL). Stir for 12 hours. Filter the suspension through a pad of silica gel and elute with ethyl acetate (500 mL). Evaporate half of the solvent and wash the remaining solution with 10% aqueous LiCl (100 mL). Dry with MgSO4 and evaporate solvent. Chromatograph the residue on a SiO2 column eluting with hexane to give 9.5 g of 1-methylsulfanyl-2-trifluoromethyl-benzene (88%).

Workup

  1. filtrationFilter the suspension through a pad of silica gel
  2. washelute with ethyl acetate (500 mL)
  3. customEvaporate half of the solvent
  4. washwash the remaining solution with 10% aqueous LiCl (100 mL)
  5. dry with materialDry with MgSO4
  6. customevaporate solvent
  7. washChromatograph the residue on a SiO2 column eluting with hexane

Sources & evidence

ORD record
ord-1dcc37024a1b4713881d06f1f0f0ff72
Source dataset
uspto-grants-2009_09
Patent number
US07585977B2

Reaction notes

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