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

HRID 1739568Notes

Reaction equation

HRID 1739568 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[Si:10](Cl)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11].N1C=CN=C1.[Cl-].[NH4+]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 115713,5-DichlorophenolHCID 25517Ammonium ChlorideHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 18007485Tert-butyl(3,5-dichlorophenoxy)dimethylsilaneYield 105.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 5.02 g of 3,5-dichlorophenol, 5.57 g of tert-butyldimethylsilyl chloride, 5.24 g of imidazole and 50 ml of N,N-dimethylformamide was stirred at 20° C. for 3 hours and then was poured into a saturated solution of ammonium chloride and extracted with dichloromethane. The organic phase was dried over magnesium sulfate and concentrated under reduced pressure to obtain 9 g of residue is obtained which was chromatographed on silica, eluant: essence G with 1/00 of triethylamine to obtain 7.45 g of the expected product.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-800fed2431d4430a8634169ccab72236
Source dataset
uspto-grants-1999_10
Patent number
US05965763

Reaction notes

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