Chlorosulfonic acid → 4-Bromo-2,5-di(propan-2-yl)benzene-1-sulfonyl chloride

HRID 1973537Notes

Reaction equation

HRID 1973537 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[CH:11]([CH3:13])[CH3:12].[Cl:14][S:15](O)(=[O:17])=[O:16]>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[C:3]([CH:11]([CH3:13])[CH3:12])=[CH:4][C:5]([S:15]([Cl:14])(=[O:17])=[O:16])=[C:6]([CH:8]([CH3:9])[CH3:10])[CH:7]=1

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 119589802,5-Diisopropyl-1-bromo-benzene

Product 1

HCID 214920504-Bromo-2,5-di(propan-2-yl)benzene-1-sulfonyl chloride

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a one-liter flask containing 80 parts of 2-bromo-1,4-diisopropylbenzene in 320 parts of carbon tetrachloride, there is added over 15 min. 154 parts of chlorosulfonic acid. After stirring thirty min. longer, the reaction mixture is poured onto 1000 parts of ice. The organic layer is separated and washed with 200 parts of water and then dried over magnesium sulfate. Removal of the solvent under reduced pressure gives 105 parts of 4-bromo-2,5-diisopropylbenzenesulfonyl chloride which can be recrystallized from n-hexane, m.p. 80°-83°.

Workup

  1. additionis added over 15 min
  2. additionthe reaction mixture is poured onto 1000 parts of ice
  3. customThe organic layer is separated
  4. washwashed with 200 parts of water
  5. dry with materialdried over magnesium sulfate
  6. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-7e974b47a08b4f6fb4a97fdc00de500d
Source dataset
uspto-grants-1976_12
Patent number
US03997603

Reaction notes

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