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

HRID 894019Notes

Reaction equation

HRID 894019 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-0b1cc0a2924a4672b520eecd199159f4
Source dataset
uspto-grants-1981_08
Patent number
US04282242

Reaction notes

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