Imidazole → Tert-butyl(3,5-dichlorophenoxy)dimethylsilane

HRID 1514992Notes

Reaction equation

HRID 1514992 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([Cl:8])[CH:7]=1.N1C=CN=C1.[CH3:15][C:16]([Si:19](Cl)([CH3:21])[CH3:20])([CH3:18])[CH3:17]>CN(C=O)C>[C:16]([Si:19]([O:9][C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=1)([CH3:21])[CH3:20])([CH3:18])([CH3:17])[CH3:15]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 115713,5-DichlorophenolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 18007485Tert-butyl(3,5-dichlorophenoxy)dimethylsilane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3,5-dichlorophenol (1.63 g, 10 mmol) and imidazole (1.50 g, 22 mmol) in DMF (10 mL) was cooled to 0° C. then TBDMSCl (1.66 g, 11 mmol) was added. After the addition, the solution was warmed up to ambient temperature and stirred for 10 min. The solution was re-cooled to 0° C. and the mixture was quenched with water. The aqueous layer was extracted with Et2O and the combined organic layers were washed with water, brine, dried with MgSO4 and filtered. The solvent was removed under reduced pressure and the residue was purified by flash chromatography using heptane/EtOAc (15:1) as eluent to give tert-butyl-(3,5-dichlorophenoxy)-dimethylsilane as a pale yellow solid.

Workup

  1. additionAfter the addition
  2. temperatureThe solution was re-cooled to 0° C.
  3. customthe mixture was quenched with water
  4. extractionThe aqueous layer was extracted with Et2O
  5. washthe combined organic layers were washed with water, brine
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. customThe solvent was removed under reduced pressure
  9. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-7c699da0f4604934bbe946a196139eed
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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