Imidazole → (2-Bromoethoxy)-tert-butyldimethylsilane

HRID 220196Notes

Reaction equation

HRID 220196 reaction equation
[Br:1][CH2:2][CH2:3][OH:4].N1C=CN=C1.[Si:10](Cl)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11].O>CN(C=O)C.C(OCC)C>[Br:1][CH2:2][CH2:3][O:4][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 108982-BromoethanolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilane

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

2-bromoethanol (10.0 mL, 141 mmol) was added to a mixture of imidazole (12.5 g, 184 mmol) and tert-butyldimethylsilyl chloride (21.1 g, 140 mmol) in anhydrous DMF (25 mL). The reaction mixture was stirred at room temperature for 12 h, water and diethyl ether were added. The phases were separated. The aqueous phase was extracted with diethyl ether. The organic phase was washed with water and brine. The solution was dried with Na2SO4. Evaporation of the solvent yielded a colorless liquid. MS: calc'd 239 (MH+), exp 239 (MH+).

Workup

  1. customThe phases were separated
  2. extractionThe aqueous phase was extracted with diethyl ether
  3. washThe organic phase was washed with water and brine
  4. dry with materialThe solution was dried with Na2SO4
  5. customEvaporation of the solvent
  6. customyielded a colorless liquid

Sources & evidence

ORD record
ord-16b67bf303914252bea68466cbb61b29
Source dataset
uspto-grants-2012_06
Patent number
US08202866B2

Reaction notes

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