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

HRID 412447Notes

Reaction equation

HRID 412447 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 min. 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 washed with a 50% saturated aqueous solution of sodium chloride (4×100 mL), dried (magnesium sulphate), 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. washThe combined organic phases were washed with a 50% saturated aqueous solution of sodium chloride (4×100 mL)
  3. dry with materialdried (magnesium sulphate)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7c2d53f115284b089a8846ed368d83cd
Source dataset
uspto-grants-2003_05
Patent number
US06562807B2

Reaction notes

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