(Trimethylsilyl)imidazole → [1-(3-Bromo-phenyl)-2,2-dimethyl-propoxy]-trimethyl-silane

HRID 546832Notes

Reaction equation

HRID 546832 reaction equation
[CH3:1][Si:2]([CH3:9])([CH3:8])N1C=CN=C1.[Br:10][C:11]1[CH:12]=[C:13]([CH:17]([OH:22])[C:18]([CH3:21])([CH3:20])[CH3:19])[CH:14]=[CH:15][CH:16]=1>O1CCCC1>[Br:10][C:11]1[CH:12]=[C:13]([CH:17]([O:22][Si:2]([CH3:1])([CH3:8])[CH3:9])[C:18]([CH3:20])([CH3:19])[CH3:21])[CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 28925(Trimethylsilyl)imidazoleHCID 574434831-(3-Bromophenyl)-2,2-dimethylpropan-1-ol

Product 1

HCID 57709209[1-(3-Bromo-phenyl)-2,2-dimethyl-propoxy]-trimethyl-silaneYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-trimethylsilylimidazole (9.5 mL, 64.86 mol) was added to a solution of the crude 1-(3-bromo-phenyl)-2,2-dimethyl-propan-1-ol in tetrahydrofuran (100 mL) in a nitrogen atmosphere at room temperature, and the mixture was stirred overnight. The reaction mixture was poured into distilled water, followed by extraction with dichloromethane. The extract was washed with brine and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel chromatography (hexane:ethyl acetate=20:1) to give the title compound as a colorless oil (11.0 g, 64% in two steps).

Workup

  1. additionThe reaction mixture was poured
  2. distillationinto distilled water
  3. extractionfollowed by extraction with dichloromethane
  4. washThe extract was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-bbe920939780486e8e1f0e9f6d75dbfe
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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