Imidazole → (5)-[1-(2-Bromo-phenyl)-ethoxy]-tert-butyl-dimethyl-silane

HRID 1592717

Reaction equation

HRID 1592717 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C@@H:4]([OH:6])[CH3:5].[Si:11](Cl)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].N1C=CN=C1>>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C@@H:4]([O:6][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])[CH3:5]

Participants

4

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 69503311-(2-Bromophenyl)ethan-1-ol

Product 1

HCID 125465295(5)-[1-(2-Bromo-phenyl)-ethoxy]-tert-butyl-dimethyl-silaneYield 82%

Procedure

To a 25 mL flask containing (S)-(−)-2-bromo-alpha-methylbenzyl alcohol (200 mg, 1.0 mmol), tert-butyldimethylsilyl chloride (165 mg, 1.1 mmol), and imidazole (203 mg, 3.0 mmol) flushed with nitrogen was added 5 mL of dimethylformamide. After stirring overnight, the mixture was quenched with saturated sodium bicarbonate, diluted with ethyl acetate, washed with NaH2PO4, saturated aqueous sodium bicarbonate, water, brine, dried (Na2SO4), filtered, and concentrated. Purification by flash chromatography (10 g SiO2, linear gradient 0-10% ethyl acetate/Hexanes, 30 mL/minute, over 30 minutes) gave about 260 mg (0.82 mmol, 82%) of (5)-[1-(2-Bromo-phenyl)-ethoxy]-tert-butyl-dimethyl-silane as a colorless oil. GC/MS (EI): 315 (M). The (5)-[1-(2-Bromo-phenyl)-ethoxy]-tert-butyl-dimethyl-silane was coupled to piperazine in a manner similar to Preparation 1A. LRMS (ESI+): 321.5 (M+1)

Workup

  1. customflushed with nitrogen
  2. additionwas added 5 mL of dimethylformamide
  3. customthe mixture was quenched with saturated sodium bicarbonate
  4. additiondiluted with ethyl acetate
  5. washwashed with NaH2PO4, saturated aqueous sodium bicarbonate, water, brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by flash chromatography (10 g SiO2, linear gradient 0-10% ethyl acetate/Hexanes, 30 mL/minute, over 30 minutes)

Sources & evidence

ORD record
ord-68095268d655410ea896a566a67e6eeb
Source dataset
uspto-grants-2007_11
Patent number
US07291619B2

Linked notes

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