Imidazole → 4-[2-(Tert-butyldimethylsilanyloxy)ethoxy]bromobenzene

HRID 1387134Notes

Reaction equation

HRID 1387134 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([O:6][CH2:7][CH2:8][OH:9])=[CH:4][CH:3]=1.[Si:12](Cl)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13].N1C=CN=C1>CN(C=O)C>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([O:6][CH2:7][CH2:8][O:9][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 991682-(p-Bromophenoxy)ethanol

Product 1

HCID 150978074-[2-(Tert-butyldimethylsilanyloxy)ethoxy]bromobenzeneYield 99.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(4-bromophenoxy)ethanol (10.94 g, 50.4 mmol), in dry DMF (50 mL), was added t-butyldimethylsilyl chloride (7.6 g , 50.4 mmol) and imidazole (3.77 g , 55.5 mmol). The reaction was stirred at ambient temperature for 18 h, then partitioned with hexane (300 mL) and water (300 mL). The aqueous layer was extracted with hexane (3×100 mL). The combined organic extracts were dried (MgSO4) and the solvent removed under reduced pressure to give the desired product as an oil (16.6 g, 99%).

Workup

  1. custompartitioned with hexane (300 mL) and water (300 mL)
  2. extractionThe aqueous layer was extracted with hexane (3×100 mL)
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-ee293c3bdccf400b9a6af00191d49d87
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Reaction notes

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