Water → 1-(Methylthio)-2-(trifluoromethoxy)benzene

HRID 1633937Notes

Reaction equation

HRID 1633937 reaction equation
CI.[C:3](=O)([O-])[O-].[K+].[K+].[F:9][C:10]([F:20])([F:19])[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[SH:18].O>CN(C=O)C>[CH3:3][S:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[O:11][C:10]([F:9])([F:19])[F:20]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 27607322-(Trifluoromethoxy)thiophenol

Product 1

HCID 27815671-(Methylthio)-2-(trifluoromethoxy)benzeneYield 90.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl iodide (59.0 g, 0.41 mol) in DMF (150 mL) was added potassium carbonate (23.0 g, 0.16 mol). 2-(Trifluoromethoxy)thiophenol (16.0 g, 0.08 mol) was added in portions during 30 minutes. The reaction mixture was then stirred vigorously overnight. Water (250 mL) was added. The reaction mixture was extracted with ethyl acetate (2×150 mL). The combined organic phases were extracted with a 50% saturated aqueous solution of sodium chloride (4×100 mL), dried (MgSO4), and concentrated in vacuo to give 15.0 g of 1-methylsulfanyl-2-trifluoromethoxybenzene.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate (2×150 mL)
  2. extractionThe combined organic phases were extracted with a 50% saturated aqueous solution of sodium chloride (4×100 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a02848819e29437796a1a6450e27b0e5
Source dataset
uspto-grants-2003_01
Patent number
US06503949B1

Reaction notes

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