Chloride → 1-(Methanesulfonyl)-4-(trichloromethyl)benzene

HRID 1979656Notes

Reaction equation

HRID 1979656 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8](C)=[CH:7][CH:6]=1)(=[O:4])=[O:3].ClCl.Cl=O.[Cl-].[C:17]([Cl:21])(Cl)([Cl:19])[Cl:18]>>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:17]([Cl:21])([Cl:19])[Cl:18])=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

6

Reactant 5

HCID 312ChlorideHCID 5943Carbon TetrachlorideHCID 18521p-Tolyl methyl sulfoneHCID 24526Chlorine2×HCID 166686Chlorine oxide (ClO)

Product 1

HCID 204379571-(Methanesulfonyl)-4-(trichloromethyl)benzene

Procedure

Methyl p-tolylsulfone (100 g, 0.59 mole), carbon tetrachloride (1500 ml) and mercuric oxide (211 g) were added to a 3-necked flask equipped with a mechanical stirrer, gas inlet, dry-ice condenser and thermometer. The mixture was stirred and maintained at 50°-60° while adding chlorine gas (scrubbed through sulfuric acid) at a rate of approximately 1600 cc/min for 35 minutes (155 g). At this point chlorine monoxide started refluxing and chloride addition was discontinued. The mixture was stirred and heated for a total of 7 hours and additional chlorine (65 g) and mercuric oxide (100 g) were added as needed to complete the reaction which can be readily monitored by N-nmr.

Workup

  1. customequipped with a mechanical stirrer, gas inlet, dry-ice condenser
  2. temperaturemaintained at 50°-60°
  3. stirringThe mixture was stirred
  4. additionwere added
  5. customthe reaction which

Sources & evidence

ORD record
ord-d886ea173c8c41769aae3cab0531a11d
Source dataset
uspto-grants-1984_11
Patent number
US04482371

Reaction notes

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