Imidazole → Tert-butyl(2,4-dichlorophenoxy)dimethylsilane

HRID 2235207Notes

Reaction equation

HRID 2235207 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[OH:9].N1C=CN=C1.[Si:15](Cl)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]>O>[C:18]([Si:15]([O:9][C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[Cl:1])([CH3:17])[CH3:16])([CH3:21])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 84492,4-DichlorophenolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 59803885Tert-butyl(2,4-dichlorophenoxy)dimethylsilaneYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve 2,4-dichloro-phenol (30 g, 184 mmol) and cool to 0° C. Add imidazole (28 g, 405 mmol) followed by t-butyldimethylsilyl chloride (31 g, 202 mmol). Warm reaction mixture to room temperature, and stir for 20 minutes. Pour reaction mixture into water and extract with ether. Separate layers and wash organics with water, 2× brine, dry over sodium sulfate, filter and concentrate to yield 48.4 g (95%) of tert-butyl-(2,4-dichloro-phenoxy)-dimethyl-silane.

Workup

  1. temperatureWarm
  2. customreaction mixture to room temperature
  3. additionPour
  4. extractionextract with ether
  5. washSeparate layers and wash organics with water, 2× brine
  6. dry with materialdry over sodium sulfate
  7. filtrationfilter
  8. concentrationconcentrate

Sources & evidence

ORD record
ord-ddb2a7d4602d40f4bbdf514548c22aa6
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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