2-Bromoethanol → (2-Bromoethoxy)-tert-butyldimethylsilane

HRID 1522880Notes

Reaction equation

HRID 1522880 reaction equation
[Br:1][CH2:2][CH2:3][OH:4].[CH3:5][C:6]([Si:9](Cl)([CH3:11])[CH3:10])([CH3:8])[CH3:7]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Br:1][CH2:2][CH2:3][O:4][Si:9]([C:6]([CH3:8])([CH3:7])[CH3:5])([CH3:11])[CH3:10]

Participants

5

Reactant 2

HCID 108982-BromoethanolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilane

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-bromo-ethanol (12.5 g, 0.1 mol) and TEA (11.2 g, 0.11 mol) in CH2Cl2 (40 mL), TBSCl (15.8 g, 0.105 mol) and DMAP (0.122 g, 1 mmol) were added. The reaction mixture was stirred at room temperature for 12 h, washed (10 mL 2M HCl, 10 mL H2O), dried (Na2SO4) and concentrated to give the desired product as colorless oil. 1H NMR (CDCl3): δ 3.88 (m, 2H), 3.39 (m, 2H), 0.89 (s, 9H), 0.08 (s, 6H).

Workup

  1. additionwere added
  2. washwashed (10 mL 2M HCl, 10 mL H2O)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a924e5f7d10c42c791c1c9966a6b88ac
Source dataset
uspto-grants-2015_07
Patent number
US09078871B2

Reaction notes

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