Imidazole → Tert-butyl-(5-ethoxy-2-fluoro-phenoxy)-dimethyl-silane

HRID 478963Notes

Reaction equation

HRID 478963 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]([F:11])=[C:8]([OH:10])[CH:9]=1)[CH3:2].[C:12]([Si:16]([CH3:19])([CH3:18])Cl)([CH3:15])([CH3:14])[CH3:13].N1C=CN=C1.O>CC(N(C)C)=O>[C:12]([Si:16]([O:10][C:8]1[CH:9]=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=[CH:6][C:7]=1[F:11])([CH3:19])[CH3:18])([CH3:15])([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 180033705-Ethoxy-2-fluorophenol

Product 1

HCID 18003379Tert-butyl-(5-ethoxy-2-fluoro-phenoxy)-dimethyl-silaneYield 97.1%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of 75.5 g 5-ethoxy-2-fluoro-phenol described in example 1.1 in 250 ml DMA were added 80.2 g t-butyl dimethylchlorsilane and 36.2 g imidazole at 0° C. The reaction mixture was warmed to r.t. After 4 hrs, 400 ml water were added. The mixture was extracted with hexane. The organic layer was washed with water, 10% Na2CO3 solution, water and brine, dried over MgSO4, filtrated and concentrated to give 127.0 g tert-butyl-(5-ethoxy-2-fluoro-phenoxy)-dimethyl-silane as light brown liquid which was used in the next step without further purification.

Workup

  1. extractionThe mixture was extracted with hexane
  2. washThe organic layer was washed with water, 10% Na2CO3 solution, water and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltrated
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-34750469404c4351ae2a49431a94c31b
Source dataset
uspto-grants-2003_11
Patent number
US06642386B2

Reaction notes

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