Chlorosulfonic acid → 5-(2,6-Dichloro-4-trifluoromethylphenyl)-2-methylbenzenesulfonyl chloride

HRID 25301Notes

Reaction equation

HRID 25301 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1.[Cl:20][S:21](O)(=[O:23])=[O:22]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:5]=[C:4]([Cl:12])[C:3]=1[C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[C:15]([S:21]([Cl:20])(=[O:23])=[O:22])[CH:14]=1

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 221709614-(2,6-Dichloro-4-trifluoromethylphenyl)toluene

Product 1

HCID 221709435-(2,6-Dichloro-4-trifluoromethylphenyl)-2-methylbenzenesulfonyl chlorideYield 81.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

6.7 g (22.0 mmol) of 4-(2,6-dichloro-4-trifluoromethylphenyl)toluene prepared in (a) was dissolved in 50 ml of chloroform, and 3.8 g (32.6 mmol) of chlorosulfonic acid was added dropwise at 0° C. with stirring. After further 3 hours of stirring at room temperature, the reaction mixture was poured into about 200 ml of ice-cold water for separation. The organic layer was washed with water twice and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 7.2 g of 5-(2,6-dichloro-4-trifluoromethylphenyl)-2-methylbenzenesulfonyl chloride (yield 81.0%).

Workup

  1. stirringAfter further 3 hours of stirring at room temperature
  2. washThe organic layer was washed with water twice
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-9aa8631c2eb64e40b3b9fd6dd9f8e030
Source dataset
uspto-grants-2005_02
Patent number
US06858639B2

Reaction notes

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