Chlorosulfonic acid → HCID 86625712, compound

HRID 1662731Notes

Reaction equation

HRID 1662731 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][C:10]([F:13])([F:12])[F:11])[CH:4]=1.[Cl:14][S:15]([OH:18])(=[O:17])=[O:16]>C(Cl)(Cl)Cl>[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([S:15]([Cl:14])(=[O:17])=[O:16])=[C:5]([O:9][C:10]([F:11])([F:12])[F:13])[CH:4]=1.[CH3:1][S:2][C:3]1[CH:4]=[C:5]([O:9][C:10]([F:11])([F:12])[F:13])[CH:6]=[CH:7][C:8]=1[S:15]([Cl:14])(=[O:18])=[O:16]

Participants

5

Reactant 2

HCID 24638Chlorosulfonic acidHCID 67428671HCID 67428671, compound

Product 2

HCID 86625712HCID 86625712, compoundHCID 86625713HCID 86625713, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 1.00 g of the compound obtained in Step 179-1 in CHCl3 (10 ml) was added dropwise 3.36 g of chlorosulfonic acid in CHCl3 (10 ml) over 30 minutes under ice cooling. After stirring at room temperature for one hour, the solution was poured into ice water and the resulting mixture was extracted with CHCl3. The organic layer was washed with a saturated aqueous solution of NaHCO3 and with saturated brine and then dried over MgSO4; the drying agent was separated by filtration, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography (silicagel 60N; mobile phase: EtOAc/n-hexane=1/10 to 1/5; v/v) to obtain 340 mg of 4-(methylthio)-2-(trifluoromethoxy)benzene sulfonyl chloride (179-2-a) and 212 mg of 2-(methylthio)-4-(trifluoromethoxy)benzene sulfonyl chloride (179-2-b).

Workup

  1. extractionthe resulting mixture was extracted with CHCl3
  2. washThe organic layer was washed with a saturated aqueous solution of NaHCO3 and with saturated brine
  3. dry with materialdried over MgSO4
  4. customthe drying agent was separated by filtration
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by column chromatography (silicagel 60N; mobile phase: EtOAc/n-hexane=1/10 to 1/5; v/v)

Sources & evidence

ORD record
ord-cae0664ff36c4cb4a839c2ec3e233759
Source dataset
uspto-grants-2011_10
Patent number
US08030499B2

Reaction notes

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