Imidazole → 4-Bromobenzyloxy-tert-butyldimethylsilane

HRID 1890631Notes

Reaction equation

HRID 1890631 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.[Si:10](Cl)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11].N1C=CN=C1>CN(C=O)C>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][O:7][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 701194-Bromobenzyl alcohol

Product 1

HCID 108595834-Bromobenzyloxy-tert-butyldimethylsilaneYield 85.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Commercially available 4-bromobenzylalcohol (4.00 g, 21.5 mmol) was dissolved in DMF (100 mL), and tert-butyldimethylsilyl chloride (4.86 g, 32.2 mmol) and imidazole (2.20 g, 32.3 mmol) were added to the solution, followed by stirring at room temperature for 1.5 hours. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in ethyl acetate. The solution was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate, then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:80) to obtain 4-bromobenzyloxy-tert-butyldimethylsilane (5.52 g, yield 85%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe solution was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:80)

Sources & evidence

ORD record
ord-1b1d27f44eb348e5923fca34be6f3a5e
Source dataset
uspto-grants-2013_08
Patent number
US08507484B2

Reaction notes

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