Chlorosulfonic acid → 2,5-Dichloro-4-methylbenzene-1-sulfonyl chloride

HRID 1167247Notes

Reaction equation

HRID 1167247 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[CH3:9].[Cl:10][S:11](O)(=[O:13])=[O:12]>>[Cl:8][C:5]1[CH:4]=[C:3]([CH3:9])[C:2]([Cl:1])=[CH:7][C:6]=1[S:11]([Cl:10])(=[O:13])=[O:12]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 295722,5-Dichlorotoluene

Product 1

HCID 134912212,5-Dichloro-4-methylbenzene-1-sulfonyl chlorideYield 88%

Conditions

Temperature
0 °C

Procedure

A dry flask under argon was charged with chlorosulfonic acid (30 mL) and cooled to 0° C. 2,5-Dichlorotoluene (10 g, 62.1 mmol) was then added dropwise, and once the addition was complete, the reaction was heated to 60° C. and stirred for 30 min. After cooling to room temperature, the reaction mixture was poured slowly onto ice. The aqueous mixture was extracted twice with methylene chloride, and the organics were dried and concentrated to provide 2,5-dichloro-4-methylbenzenesulfonyl chloride (14.14 g, 88%) as a white solid.

Workup

  1. additiononce the addition
  2. temperaturethe reaction was heated to 60° C.
  3. temperatureAfter cooling to room temperature
  4. additionthe reaction mixture was poured slowly onto ice
  5. extractionThe aqueous mixture was extracted twice with methylene chloride
  6. customthe organics were dried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4aa8bc8e7f39416b9f73f8c00afc4573
Source dataset
uspto-grants-2003_09
Patent number
US06617357B2

Reaction notes

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