Imidazole → {[3-(3-Bromo-4-fluorophenyl)but-3-en-1-yl]oxy}(tert-butyl)dimethylsilane

HRID 446592Notes

Reaction equation

HRID 446592 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9](=[CH2:13])[CH2:10][CH2:11][OH:12])[CH:5]=[CH:6][C:7]=1[F:8].N1C=CN=C1.[C:19]([Si:23](Cl)([CH3:25])[CH3:24])([CH3:22])([CH3:21])[CH3:20].O>C(Cl)Cl.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:9](=[CH2:13])[CH2:10][CH2:11][O:12][Si:23]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:25])[CH3:24])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 66671565HCID 66671565, compound

Product 1

HCID 66671495{[3-(3-Bromo-4-fluorophenyl)but-3-en-1-yl]oxy}(tert-butyl)dimethylsilaneYield 95%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The compound (2.17 g, 8.85 mmol) obtained in Example 91b was dissolved in methylene chloride (33 mL), imidazole (0.90 g, 13.3 mmol) and tert-butyl(chloro)dimethylsilane (1.60 g, 10.6 mmol) were added with stirring under ice cooling, and the mixture was stirred at room temperature under a nitrogen atmosphere for 20 hours. After the reaction was completed, water was added, and ethyl acetate was further added to separate the layers. The resulting organic layer was separated, washed with saturated sodium chloride solution, and then dried with anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:1, v/v) to give the title compound (3.02 g; yield, 95%) as a colorless oily substance.

Workup

  1. stirringthe mixture was stirred at room temperature under a nitrogen atmosphere for 20 hours
  2. customto separate the layers
  3. customThe resulting organic layer was separated
  4. washwashed with saturated sodium chloride solution
  5. dry with materialdried with anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:1, v/v)

Sources & evidence

ORD record
ord-9a12f0e9d24b489baa8e4783599549eb
Source dataset
uspto-grants-2013_07
Patent number
US08476253B2

Reaction notes

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