Triethylamine → (2-Bromoethoxy)-tert-butyldimethylsilane

HRID 1656292Notes

Reaction equation

HRID 1656292 reaction equation
[Br:1][CH2:2][CH2:3][OH:4].[C:5]([Si:9]([CH3:12])([CH3:11])Cl)([CH3:8])([CH3:7])[CH3:6].C(N(CC)CC)C>C(Cl)Cl.CN(C1C=CC=CN=1)C>[Si:9]([O:4][CH2:3][CH2:2][Br:1])([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:12])[CH3:11]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 108982-BromoethanolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneYield 88.8%

Reagents, catalysts & solvents 2

HCID 218852-DimethylaminopyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-bromoethanol (50 g, 0.40 mol) in CH2Cl2 (50 mL) was added t-butyldimethylchlorosilane (63.4 g, 0.42 mol), triethylamine (45.4 g, 0.45 mol) and dimethylaminopyridine (0.5 g). After stirring overnight the reaction mixture was washed 3× with water. The organic fraction was dried with Na2SO4, filtered, and concentrated in vacuo to provide 85 g of the title compound as a light yellow oil.

Workup

  1. washwas washed 3× with water
  2. dry with materialThe organic fraction was dried with Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-69993f00f0534ae8ae31ae8f3d5eb24a
Source dataset
uspto-grants-1993_10
Patent number
US05252732

Reaction notes

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