Water → Methyl 2-methylsulphonyl-3-phenylsulphenylbenzoate

HRID 1491580Notes

Reaction equation

HRID 1491580 reaction equation
F[C:2]1[C:3]([S:12]([CH3:15])(=[O:14])=[O:13])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].C(=O)([O-])[O-].[K+].[K+].[C:22]1([SH:28])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.O>CN(C)C=O.C(OCC)(=O)C>[CH3:15][S:12]([C:3]1[C:2]([S:28][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:11][CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6])(=[O:14])=[O:13]

Participants

7

Reactant 4

HCID 962WaterHCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 18953324Methyl 3-fluoro-2-methylsulphonylbenzoate

Product 1

HCID 18953302Methyl 2-methylsulphonyl-3-phenylsulphenylbenzoateYield 46.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of methyl 3-fluoro-2-methylsulphonylbenzoate (10.9 g), potassium carbonate (7.8 g) and thiophenol (5.4 g) in N,N-dimethylformamide was stirred at 25° C. for six hours. Water and ethyl acetate were added and the resulting solid collected by filtration and combined with the solid obtained from washing the organic phase of the flitrate with brine, drying over magnesium sulphate, filtering and evaporating. This product was recrystallised from ethyl acetate to give 7.0 g of methyl 2-methylsulphonyl-3-phenylsulphenylbenzoate as white crystals, mp 151.1° C.

Workup

  1. filtrationthe resulting solid collected by filtration
  2. customobtained
  3. washfrom washing the organic phase of the flitrate with brine
  4. dry with materialdrying over magnesium sulphate
  5. filtrationfiltering
  6. customevaporating
  7. customThis product was recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-09af85754802491ebebb86024e751be8
Source dataset
uspto-grants-1994_12
Patent number
US05371064

Reaction notes

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