Imidazole → tert-Butyl(5-ethyl-2-fluorophenoxy)dimethylsilane

HRID 1157939Notes

Reaction equation

HRID 1157939 reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([F:10])=[C:7]([OH:9])[CH:8]=1)[CH3:2].N1C=CN=C1.[C:16]([Si:20]([CH3:23])([CH3:22])Cl)([CH3:19])([CH3:18])[CH3:17].C(OCC)C>CN(C=O)C.O>[C:16]([Si:20]([O:9][C:7]1[CH:8]=[C:3]([CH2:1][CH3:2])[CH:4]=[CH:5][C:6]=1[F:10])([CH3:23])[CH3:22])([CH3:19])([CH3:18])[CH3:17]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 3283Diethyl EtherHCID 28928tert-Butyldimethylsilyl chlorideHCID 187116495-Ethyl-2-fluorophenol

Product 1

HCID 59838026tert-Butyl(5-ethyl-2-fluorophenoxy)dimethylsilaneYield 85.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a 40 ml solution of 16.4 g of 5-ethyl-2-fluorophenol in DMF there were added 9.16 g of imidazole and 19.4 g of t-butyldimethylchlorosilane, and the reaction mixture was stirred at room temperature for 18 hours. After then adding 500 ml of diethyl ether and 500 ml of water to the reaction mixture, the organic layer was washed twice with 100 ml of water and once with 100 ml of saturated aqueous sodium chloride in that order and then dried over anhydrous magnesium sulfate, the desiccant was filtered out, and the filtrate was concentrated under reduced pressure. The residue was distilled to obtain the target compound (25.38 g) as a colorless liquid (boiling point: 133-135° C., 20 mmHg).

Workup

  1. washthe organic layer was washed twice with 100 ml of water and once with 100 ml of saturated aqueous sodium chloride in that order
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationthe desiccant was filtered out
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. distillationThe residue was distilled

Sources & evidence

ORD record
ord-98a2e7216817404994971e7877b39e56
Source dataset
uspto-grants-2010_10
Patent number
US07807690B2

Reaction notes

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