Imidazole → [2-(4-Bromophenyl)ethoxy](tert-butyl)dimethylsilane

HRID 2190339Notes

Reaction equation

HRID 2190339 reaction equation
N1C=CN=C1.[Br:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][OH:15])=[CH:9][CH:8]=1.[C:16]([Si:20](Cl)([CH3:22])[CH3:21])([CH3:19])([CH3:18])[CH3:17]>C1COCC1>[Br:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][O:15][Si:20]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:22])[CH3:21])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 728512-(4-Bromophenyl)ethanol

Product 1

HCID 23254500[2-(4-Bromophenyl)ethoxy](tert-butyl)dimethylsilane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1H-imidazole (1.06 g, 15.6 mmol) and 2-(4-bromophenyl)ethanol (2.19 g, 10.9 mmol) in THF (20 mL) at room temperature was added tert-butylchlorodimethylsilane (1.81 g, 12.0 mmol). The reaction mixture was stirred at room temperature for 2 h and diluted with hexanes. The organic phase was washed with water (2×), brine (1×), dried over MgSO4, filtered, and concentrated to give (4-bromophenethoxy)(tert-butyl)dimethylsilane 65 which was used in the next step without further purification.

Workup

  1. washThe organic phase was washed with water (2×), brine (1×)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9f75562e8c0e487d818e9d1d56683e9d
Source dataset
uspto-grants-2012_12
Patent number
US08324396B2

Reaction notes

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