Imidazole → (3-Bromophenethoxy)(tert-butyl)dimethylsilane

HRID 2117957Notes

Reaction equation

HRID 2117957 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][OH:10])[CH:5]=[CH:6][CH:7]=1.[Si:11](Cl)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].N1C=CN=C1.O>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 27340902-(3-Bromophenyl)ethan-1-ol

Product 1

HCID 11515183(3-Bromophenethoxy)(tert-butyl)dimethylsilane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 2-(3-bromophenyl)ethanol (7 g) in N,N-dimethylformamide (100 ml) were added tert-butyldimethylsilyl chloride (5.77 g) and imidazole (2.84 g) at 25° C. The mixture was stirred at 25° C. for 12 h. The reaction mixture was poured into water (500 ml) and extracted with ethyl acetate (100 ml×2). The combined organic layer was dried over magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography with mixed solvent of n-hexane and ethyl acetate to give [2-(3-bromophenyl)ethoxy](tert-butyl)dimethylsilane as colorless oil.

Workup

  1. extractionextracted with ethyl acetate (100 ml×2)
  2. dry with materialThe combined organic layer was dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel column chromatography with mixed solvent of n-hexane and ethyl acetate

Sources & evidence

ORD record
ord-07e2da3cdd5d4dea9a02c53ac1588dc8
Source dataset
uspto-grants-2008_10
Patent number
US07442715B2

Reaction notes

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