Sulfuric Acid → HCID 21556755, compound

HRID 267290Notes

Reaction equation

HRID 267290 reaction equation
S(=O)(=O)(O)O.[Br:6][C:7]1[C:12]([CH:13]([CH2:15][CH3:16])[CH3:14])=[CH:11][C:10]([S:17](Cl)(=O)=O)=[C:9]([CH:21]([CH2:23][CH3:24])[CH3:22])[CH:8]=1>[Zn]>[Br:6][C:7]1[C:12]([CH:13]([CH2:15][CH3:16])[CH3:14])=[CH:11][C:10]([SH:17])=[C:9]([CH:21]([CH2:23][CH3:24])[CH3:22])[CH:8]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 21556733HCID 21556733, compound

Product 1

HCID 21556755HCID 21556755, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

A 128-ml portion of concentrated sulfuric acid was added to 300 g of ice while keeping the temperature at 0°-10°C. Then 41 g of 4-bromo-2,5-di-sec-butylbenzenesulfonyl chloride was added. While maintaining the temperature at 0°-10°C, 65 g of zinc dust was added with good agitation over a period of 2 hours. The reaction mixture was then heated under reflux on a steam bath for 5 hours. After cooling, the mixture was extracted into methylene dichloride, dried over magnesium sulfate, filtered, and concentrated to an oil which was distilled, to give 27 g of 4-bromo-2,5-di-sec-butylbenzenethiol, bp 106°-107°C/0.22 mm, nD25 1.5599.

Workup

  1. customat 0°-10°C
  2. temperatureWhile maintaining the temperature at 0°-10°C
  3. temperatureThe reaction mixture was then heated
  4. temperatureunder reflux on a steam bath for 5 hours
  5. temperatureAfter cooling
  6. extractionthe mixture was extracted into methylene dichloride
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated to an oil which
  10. distillationwas distilled

Sources & evidence

ORD record
ord-1ebf4483d0454bc588225bf5b6e85b63
Source dataset
uspto-grants-1976_03
Patent number
US03941826

Reaction notes

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