Chlorine → p-t-Butylbenzenesulfenyl chloride

HRID 1659507Notes

Reaction equation

HRID 1659507 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([SH:11])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Cl:12]Cl>C(Cl)(Cl)(Cl)Cl>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([S:11][Cl:12])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 24526Chlorine2×HCID 754544-Tert-Butylbenzenethiol

Product 1

HCID 12801136p-t-Butylbenzenesulfenyl chlorideYield 94.2%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

To a mixture of 332 grams (2.0 moles) of 4-(tert-butyl)thiophenol and 800 ml of carbon tetrachloride was slowly added with stirring and cooling a solution of 150 grams (2.0+ moles) of chlorine in 600 ml of carbon tetrachloride at 0° C. After chlorine addition was complete the mixture was stirred at 0°-10° C. for two hours, hydrogen chloride and carbon tetrachloride removed in vacuo and the residue was distilled in a one-foot packed column to give 378 grams of 4-(tert-butyl)phenylsulfenyl chloride, b.p. 95°-97°/1.0 mm (yield 94%).

Workup

  1. additionwas slowly added
  2. stirringwas stirred at 0°-10° C. for two hours
  3. customhydrogen chloride and carbon tetrachloride removed in vacuo
  4. distillationthe residue was distilled in a one-foot

Sources & evidence

ORD record
ord-6071356de80945b8a798b37b13b3a953
Source dataset
uspto-grants-1981_12
Patent number
US04304735

Reaction notes

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