Potassium Carbonate → Methyl 2-phenylsulfonylmethylthio-5-trifluoromethylbenzoate

HRID 1731300Notes

Reaction equation

HRID 1731300 reaction equation
[SH:1][C:2]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].Cl[CH2:17][S:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:19].C([O-])([O-])=[O:27].[K+].[K+]>CN(C=O)C.O>[C:20]1([S:18]([CH2:17][S:1][C:2]2[CH:11]=[CH:10][C:9]([C:12]([F:13])([F:14])[F:15])=[CH:8][C:3]=2[C:4]([O:6][CH3:7])=[O:5])(=[O:27])=[O:19])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 81624Chloromethyl phenyl sulfoxideHCID 13787739Methyl 2-mercapto-5-trifluoromethylbenzoate

Product 1

HCID 20228789Methyl 2-phenylsulfonylmethylthio-5-trifluoromethylbenzoateYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of methyl 2-mercapto-5-trifluoromethylbenzoate (0.94 g, 0.0040 moles), chloromethylphenylsulfoxide (0.70 g, 0.0040 moles) and K2CO3 (1.66 g, 0.012 moles) in DMF (10 ml) was stirred vigorously at 50° for 45 minutes. The reaction was cooled, diluted with water (30 ml), and the resulting precipitate collected, water and hexane washed, and dried under vacuum to afford 1.05 g (70%) of methyl 2-phenylsulfonylmethylthio-5-trifluoromethylbenzoate. Rf (Et2O:Hexane, 1:1+1% Acetic Acid)=0.15.

Workup

  1. temperatureThe reaction was cooled
  2. customthe resulting precipitate collected
  3. washwater and hexane washed
  4. customdried under vacuum

Sources & evidence

ORD record
ord-a2c7193cb9de425ebadeffd2b094404e
Source dataset
uspto-grants-1986_11
Patent number
US04621091

Reaction notes

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