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

HRID 1171142Notes

Reaction equation

HRID 1171142 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-27c2a7529bb04e55a40f8a60ff8c1671
Source dataset
uspto-grants-2010_11
Patent number
US07829582B2

Reaction notes

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