Chlorosuccinimide → 1-Chloro-2-(chlorosulfanyl)benzene

HRID 1703250Notes

Reaction equation

HRID 1703250 reaction equation
[Cl:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[SH:16]>C(Cl)(Cl)(Cl)Cl>[Cl:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[S:16][Cl:1]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 80599o-Chlorothiophenol

Product 1

HCID 129632401-Chloro-2-(chlorosulfanyl)benzeneYield 94.9%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

Under nitrogen, N-chlorosuccinimide (5.34 g., 40 mmoles) was slurried in 50 ml. of carbon tetrachloride and the stirred mixture cooled in an ice-water bath. o-Chlorothiophenol (5.76 g., 40 mmoles), dissolved in 25 ml. of carbon tetrachloride, was added dropwise. The ice-water bath was removed and the reaction mixture stirred at room temperature for approximately 16 hours. The reaction was filtered, evaporated to an oil, taken up in hexane, refiltered and reconcentrated to yield o-chlorobenzenesulfenyl chloride (6.8 g., oil).

Workup

  1. customThe ice-water bath was removed
  2. filtrationThe reaction was filtered
  3. customevaporated to an oil

Sources & evidence

ORD record
ord-b8dd54bfa8ec4569999c3c96b014ea06
Source dataset
uspto-grants-1982_09
Patent number
US04351843

Reaction notes

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