Chlorobenzene → 1-Chloro-4-(methylsulfonyl)benzene

HRID 247010Notes

Reaction equation

HRID 247010 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[CH3:12][S:13](Cl)(=[O:15])=[O:14]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:13]([CH3:12])(=[O:15])=[O:14])=[CH:4][CH:3]=1

Participants

5

Conditions

Temperature
15 °C

Procedure

To 600 ml of chlorobenzene were added 272 g of anhydrous aluminum chloride and 229 g of methanesulfonyl chloride and the mixture was heated on a steam bath for 6 hours with stirring. The solution thus formed was poured into ice-water, and then the produce was extracted with 400 ml of methylene chloride. Methylene chloride was distilled off from the extract under reduced pressure. To the residue thus formed was added 300 ml of methanol, the mixture was cooled to 15° C., and crystals thus deposited were collected by filtration to provide 212 g 1-chloro-4-methylsulfonyl benzene having a melting point of 92° to 94° C.

Workup

  1. temperaturethe mixture was heated on a steam bath for 6 hours
  2. customThe solution thus formed
  3. extractionthe produce was extracted with 400 ml of methylene chloride
  4. distillationMethylene chloride was distilled off from the
  5. extractionextract under reduced pressure
  6. customTo the residue thus formed
  7. filtrationcrystals thus deposited were collected by filtration

Sources & evidence

ORD record
ord-79efd36d53ed404ea33c83829ccebb1c
Source dataset
uspto-grants-1987_11
Patent number
US04705737

Reaction notes

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