Water → 1-Bromo-4-(1-methylpropylthio)benzene

HRID 1073423Notes

Reaction equation

HRID 1073423 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH:16]([CH3:19])[CH2:17][CH3:18].O>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH:16]([CH3:19])[CH2:17][CH3:18])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 65542-BromobutaneHCID 11430Potassium CarbonateHCID 660494-Bromothiophenol

Product 1

HCID 198165221-Bromo-4-(1-methylpropylthio)benzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Bromo-4-(1-methylpropylthio)benzene is prepared by the following procedure. To a solution of 4-bromobenzenethiol (4.73 g, 5.0 mmol) in 25 ml of DMF at 70° under N2 is added potassium carbonate (4.15 g, 30.0 mmol). The mixture is allowed to stir for 15 min., after which 3-bromobutane (4.8 ml, 44.0 mmol) is added dropwise. The mixture is stirred at 70° for ca. 5 hours. Water is added to the cooled solution and the aqueous phase is extracted with ether (3×). The combined organic layers are washed with water and with brine and dried and the solvent is removed in vacuo to give, following purification by distillation under vacuum, 1-bromo-4-[1-methylpropylthio)benzene.

Workup

  1. stirringThe mixture is stirred at 70° for ca. 5 hours
  2. extractionthe aqueous phase is extracted with ether (3×)
  3. washThe combined organic layers are washed with water and with brine
  4. customdried
  5. customthe solvent is removed in vacuo
  6. customto give
  7. custompurification
  8. distillationby distillation under vacuum, 1-bromo-4-[1-methylpropylthio)benzene

Sources & evidence

ORD record
ord-9671a20a63ab4fa7a59b9dedca8f01f1
Source dataset
uspto-grants-1990_11
Patent number
US04968829

Reaction notes

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