2-Bromopropane → 1-Bromo-4-(propan-2-ylsulfanyl)benzene

HRID 2103601Notes

Reaction equation

HRID 2103601 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]([CH3:18])[CH3:17]>CC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH:16]([CH3:18])[CH3:17])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 660494-Bromothiophenol

Product 1

HCID 125212401-Bromo-4-(propan-2-ylsulfanyl)benzeneYield 67.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Dissolve 4-bromo-benzenethiol (2.6 g, 13.2 mmol) in 150 mL acetone, add potassium carbonate (2.0 g, 14.5 mmol) and 2-bromo-propane (1.8 g, 14.5 mmol) and stir 2 days at r.t. Evaporate the solvent under vacuum, add water and extract with dichloromethane. Filter through a hydrophobic filter paper and concentrate. Purify the resulting material via column chromatography on silica gel, eluting with hexane:ethyl acetate 98:2 to afford the title compound as a yellow oil (2.06 g). MS (m/e): 231 [(79Br)M], 233 [(81Br)M].

Workup

  1. customEvaporate the solvent under vacuum
  2. additionadd water
  3. extractionextract with dichloromethane
  4. filtrationFilter through a hydrophobic filter paper
  5. concentrationconcentrate
  6. customPurify the resulting material via column chromatography on silica gel
  7. washeluting with hexane:ethyl acetate 98:2

Sources & evidence

ORD record
ord-679e064ec73843018af46bafe68e152f
Source dataset
uspto-grants-2009_08
Patent number
US07576108B2

Reaction notes

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