Imidazole → (2-Bromoethoxy)-tert-butyldimethylsilane

HRID 420438Notes

Reaction equation

HRID 420438 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>[Si:10]([O:4][CH2:3][CH2:2][Br:1])([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-butyldimethylsilaneYield 97%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

Following a published 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 combined organic phases were washed with water and brine. The solution was dried (Na2SO4). Evaporation of the solvent followed by bulb-to-bulb distillation (40-45° C./0.05 mmHg) yielded a colorless liquid (32.5 g, 97%): IR (film, νmax cm−1) 2951, 2859, 1471; 1H NMR δ 0.07 (s, 6H), 0.89 (s, 9H), 3.36-3.41 (m, 2H), 3.85-3.90 (m, 2H); 13C NMR δ −5.06, 18.49, 26.04, 33.45, 63.74; EI-MS 137/139, 181/183, calcd 238.0389 (C8H19BrOSi); Anal. Calcd C, 40.17; H, 8.01. Found: C, 40.55; H, 8.25.

Workup

  1. customThe phases were separated
  2. extractionThe aqueous phase was extracted with diethyl ether
  3. washThe combined organic phases were washed with water and brine
  4. dry with materialThe solution was dried (Na2SO4)
  5. customEvaporation of the solvent
  6. distillationfollowed by bulb-to-bulb distillation (40-45° C./0.05 mmHg)

Sources & evidence

ORD record
ord-eaef83b180024fd2aae7e6159e5c3ee9
Source dataset
uspto-grants-2012_01
Patent number
US08097609B2

Reaction notes

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