Water → {3-[(4-Bromophenyl)sulfanyl]propoxy}(tert-butyl)dimethylsilane

HRID 70581

Reaction equation

HRID 70581 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][CH2:9][CH2:10][O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13].[Br:19][C:20]1[CH:25]=[CH:24][C:23]([SH:26])=[CH:22][CH:21]=1.O>CN(C)C=O>[Br:19][C:20]1[CH:25]=[CH:24][C:23]([S:26][CH2:8][CH2:9][CH2:10][O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 660494-BromothiophenolHCID 607486(3-Bromopropoxy)(tert-butyl)dimethylsilane

Product 1

HCID 58452783{3-[(4-Bromophenyl)sulfanyl]propoxy}(tert-butyl)dimethylsilaneYield 95.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (4.1 g) and (3-bromopropoxy)-tert-butyldimethylsilane (4.1 g) were added to a solution of 4-bromothiophenol (3.0 g) in N,N-dimethylformamide, and the mixture was stirred at room temperature overnight. The reaction solution was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:1→20:1) to give the title compound as a colorless oil (5.5 g).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was then evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:1→20:1)

Sources & evidence

ORD record
ord-89f6114bf4d848c3aab847590a690aff
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Linked notes

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