Potassium Iodide → ((5-Bromo-2-iodobenzyl)oxy)(tert-butyl)dimethylsilane

HRID 2189134Notes

Reaction equation

HRID 2189134 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([I:10])=[C:6]([CH2:8][OH:9])[CH:7]=1.[H-].[Na+].[C:13]([Si:17]([CH3:20])([CH3:19])Cl)([CH3:16])([CH3:15])[CH3:14].[I-].[K+]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([I:10])=[C:6]([CH:7]=1)[CH2:8][O:9][Si:17]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 24758Sodium hydrideHCID 28928tert-Butyldimethylsilyl chlorideHCID 15339730(5-Bromo-2-iodophenyl)methanol

Product 1

HCID 68614586((5-Bromo-2-iodobenzyl)oxy)(tert-butyl)dimethylsilane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 9.59 mmol (5-bromo-2-iodo-phenyl)-methanol [199786-58-8] in 10 ml of N,N-dimethylformamide is added at room temperature dropwise to a mixture of 11.5 mmol of sodium hydride (60% in paraffine) in 20 ml of N,N-dimethylformamide. The mixture is stirred for 1 h at room temperature. 10.6 mmol of tert-butyl-dimethylchloro silane and 1.00 mmol of potassium iodide are added and the mixture stirred for 30 minutes at room temperature. The reaction is quenched with water and extracted with toluene. The combined organics are washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue is purified by flash chromatography (SiO2 60 F) to afford the title compound as colourless oil. Rf=0.35 (dichloromethane); Rt=11.31 (gradient II).

Workup

  1. stirringthe mixture stirred for 30 minutes at room temperature
  2. customThe reaction is quenched with water
  3. extractionextracted with toluene
  4. washThe combined organics are washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue is purified by flash chromatography (SiO2 60 F)

Sources & evidence

ORD record
ord-568568fb37db43b28eaf1c767ca00010
Source dataset
uspto-grants-2012_12
Patent number
US08324235B2

Reaction notes

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