Thioanisole → HCID 21872329, compound

HRID 743937Notes

Reaction equation

HRID 743937 reaction equation
[C:1]1([S:7][CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:9][C:10]([F:17])([F:16])[S:11]([O:14]C)(=[O:13])=[O:12].[CH3:18]CCCCC>C(Cl)Cl>[F:9][C:10]([F:17])([F:16])[S:11]([O-:14])(=[O:13])=[O:12].[CH3:8][S+:7]([CH3:18])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7520ThioanisoleHCID 8058HexaneHCID 9526Methyl triflate

Product 1

HCID 21872329HCID 21872329, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of thioanisole (2.48 g, 20 mmole) in methylene chloride (20 ml), methyl trifluoromethanesulfonate (3.28 g, 20 mmole) was added dropwise at 10° C. or below, and the mixture was refluxed for 2 hours with stirring. After cooling, the reaction solution was poured into n-hexane (75 ml), and the precipitate was filtered, washed with n-hexane and dried. The resultant crude solid (5.35 g) was recrystallized from iso-propanol to give 4.8 g of dimethylphenylsulfonium trifluoromethanesulfonate as white leaflets. m.p. 106.0°-107.2° C.

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. temperatureAfter cooling
  3. filtrationthe precipitate was filtered
  4. washwashed with n-hexane
  5. customdried
  6. customThe resultant crude solid (5.35 g) was recrystallized from iso-propanol

Sources & evidence

ORD record
ord-55faa60fdd3740799bfb6f8a48131adf
Source dataset
uspto-grants-1996_09
Patent number
US05558971

Reaction notes

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