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

HRID 2248177Notes

Reaction equation

HRID 2248177 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, 25.0 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 (3X). 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 (3X)
  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-978b526030304ac090ed38a31fd0a8a6
Source dataset
uspto-grants-1991_08
Patent number
US05037991

Reaction notes

Loading…