Imidazole → (2-(4-Bromophenyl)propoxy)(tert-butyl)dimethylsilane

HRID 735688Notes

Reaction equation

HRID 735688 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:11])[CH2:9][OH:10])=[CH:4][CH:3]=1.N1C=CN=C1.[Si:17](Cl)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH3:11])[CH2:9][O:10][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 5690622-(4-Bromophenyl)propan-1-ol

Product 1

HCID 57842594(2-(4-Bromophenyl)propoxy)(tert-butyl)dimethylsilaneYield 55.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 73B (2.34 g, 10.9 mmol) in 30 mL DMF, was added imidazole (1.11 g, 16.3 mmol) and tert-butyldimethylsilyl chloride (1.97 g, 13.1 mmol). The mixture was stirred at rt for 3 h, then was diluted with hexanes. The organic phase washed with H2O (2×) and brine, dried (Na2SO4) and concentrated. The product was purified by flash chromatography (0 to 10% EtOAc/hexanes gradient) to afford 2.00 g of 73C as a colorless oil. MS (ESI) m/z 197.1 (M-OTBS)+.

Workup

  1. washThe organic phase washed with H2O (2×) and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe product was purified by flash chromatography (0 to 10% EtOAc/hexanes gradient)

Sources & evidence

ORD record
ord-59efbb7ff6dc4d00bdb9ea274585ee2d
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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