Benzene → (2-Bromoethoxy)-tert-butyldimethylsilane

HRID 129511Notes

Reaction equation

HRID 129511 reaction equation
[CH2:1]([Br:4])[CH2:2][OH:3].N1C=CN=C1.[Si:10](Cl)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11].C1C=CC=CC=1>CN(C)C=O>[Si:10]([O:3][CH2:2][CH2:1][Br:4])([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]

Participants

6

Reactant 4

HCID 241BenzeneHCID 795ImidazoleHCID 108982-BromoethanolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2 g of ethylene bromohydrin and 2.4 g of imidazole were dissolved in 40 ml of N,N-dimethylformamide, to which 2.65 g of t-butyldimethylsilyl chloride were added at room temperature. After completion of the reaction, benzene was added, followed by washing with water and a sodium hydrogencarbonate aqueous solution and drying with anhydrous magnesium sulfate. This was filtered and the solvent was distilled off, thereby obtaining 3.60 g of the captioned compound (yield 94%).

Workup

  1. additionwere added at room temperature
  2. additionwas added
  3. washby washing with water
  4. dry with materiala sodium hydrogencarbonate aqueous solution and drying with anhydrous magnesium sulfate
  5. filtrationThis was filtered
  6. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-db310954b3954360b960c23ceecd5730
Source dataset
uspto-grants-1995_11
Patent number
US05468740

Reaction notes

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