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

HRID 1160246Notes

Reaction equation

HRID 1160246 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.[C:15]([Si:19](Cl)([CH3:21])[CH3:20])([CH3:18])([CH3:17])[CH3:16].O>CN(C)C=O>[C:15]([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])[CH3:16]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 115713,5-DichlorophenolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 18007485Tert-butyl(3,5-dichlorophenoxy)dimethylsilaneYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve 3,5 dichlorophenol (1 kg, 6.13 mol) in 3 L dimethylformamide (DMF) and cool to 0° C. Add imidazole (918.74 g, 6.75 mol), followed by tertbutyldimethylsilyl chloride (1017.13 g, 6.75 mol). Warm the mixture to room temperature and stir for 15 minutes. Pour into water (6 L) and extract with ether (4 L). Wash the organic layer with water 2 times, 10% aqueous lithium chloride solution then brine before drying over sodium sulfate. Filter and concentrate under vacuum to obtain tert-butyl-(3,5-dichloro-phenoxy)-dimethyl-silane (1700 g) as an oil.

Workup

  1. temperatureWarm the mixture to room temperature
  2. extractionextract with ether (4 L)
  3. washWash the organic layer with water 2 times, 10% aqueous lithium chloride solution
  4. dry with materialbrine before drying over sodium sulfate
  5. filtrationFilter
  6. concentrationconcentrate under vacuum

Sources & evidence

ORD record
ord-222bb03fad3c4f059c498a5be7760ee2
Source dataset
uspto-grants-2010_10
Patent number
US07816349B2

Reaction notes

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