Imidazole → [2-Bromo-1-(3-bromo-phenyl)-ethoxy]-trimethyl-silane

HRID 1160211Notes

Reaction equation

HRID 1160211 reaction equation
[Br:1][CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Br:11])[CH:6]=1)[OH:4].N1C=CN=C1.CN(C1C=CC=CN=1)C.Cl[Si:27]([CH3:30])([CH3:29])[CH3:28]>CN(C=O)C.C(=O)(O)[O-].[Na+]>[Br:1][CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Br:11])[CH:6]=1)[O:4][Si:27]([CH3:30])([CH3:29])[CH3:28]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 6397ChlorotrimethylsilaneHCID 218852-DimethylaminopyridineHCID 189385722-Bromo-1-(3-bromophenyl)ethanol

Product 1

HCID 59515460[2-Bromo-1-(3-bromo-phenyl)-ethoxy]-trimethyl-silane

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 2-Bromo-1-(3-bromo-phenyl)-ethanol (4.72 g, 16.9 mmol), imidazole (5.75 g, 84.5 mmol) and dimethylaminopyridine (1.03 g, 8.45 mmol) in DMF at 0° C. was added Chloro-trimethyl-silane (4.56 mL, 3.90 mmol) dropwise. Stirring continued at 0° C. for 2 hours and was then warmed to RT. The mixture was diluted with saturated sodium bicarbonate and extracted with ethyl acetate. The organics were washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The title compound was isolated as a yellow oil (5.85 g, quantitative). 1H NMR (300 MHz, CDCl3): 7.52 (s, 1H), 7.44 (d, 1H), 7.28-7.23 (m, 2H), 4.83 (t, 1H), 3.43 (d, 2H) 0.109 (s, 9H).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organics were washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1557c4f67529468784f58fec14d337e7
Source dataset
uspto-grants-2010_10
Patent number
US07816354B2

Reaction notes

Loading…