2,6-Dichlorotoluene → 2,4-Dichloro-3-methylbenzene-1-sulfonyl chloride

HRID 1990717Notes

Reaction equation

HRID 1990717 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH3:9].[Cl:10][S:11](O)(=[O:13])=[O:12]>>[Cl:1][C:2]1[C:3]([CH3:9])=[C:4]([Cl:8])[CH:5]=[CH:6][C:7]=1[S:11]([Cl:10])(=[O:13])=[O:12]

Participants

3

Reactant 2

HCID 83682,6-DichlorotolueneHCID 24638Chlorosulfonic acid

Product 1

HCID 157253742,4-Dichloro-3-methylbenzene-1-sulfonyl chlorideYield 85%

Procedure

10 ml of chlorosulfonic acid were dropwise added with 4.8 ml of 2,6-dichlorotoluene in two hours, under magnetic stirring at room temperature. After completion of the addition, the mixture was heated at 40° C. for two hours, thereby obtaining a purple solution, which was cooled and carefully poured into ice-water (0.5 l), stirring vigorously. The separated white solid was filtered, triturated, washed with water, dried over KOH and purified by washing with n-hexane, adding 200 ml of solvent under strong stirring. The mixture was filtered, the solid was discarded and the solvent was evaporated to dryness to obtain 2,4-dichloro-3-methyl-benzenesulfonyl chloride as a crystalline white solid. Yield: 85%.

Workup

  1. additionAfter completion of the addition
  2. temperaturethe mixture was heated at 40° C. for two hours
  3. customobtaining a purple solution, which
  4. temperaturewas cooled
  5. stirringstirring vigorously
  6. filtrationThe separated white solid was filtered
  7. customtriturated
  8. washwashed with water
  9. dry with materialdried over KOH
  10. custompurified
  11. washby washing with n-hexane
  12. additionadding 200 ml of solvent under strong stirring
  13. filtrationThe mixture was filtered
  14. customthe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-914016fb3d204dc2b3f71db600191261
Source dataset
uspto-grants-2010_01
Patent number
US07645759B2

Reaction notes

Loading…