Imidazole → 4-Bromo-2-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-1-methoxybenzene

HRID 1872689Notes

Reaction equation

HRID 1872689 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH3:11])=[C:6]([CH:9]=1)[CH2:7][OH:8].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]([O:10][CH3:11])=[C:6]([CH:9]=1)[CH2:7][O:8][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 6122985-Bromo-2-methoxybenzyl alcohol

Product 1

HCID 120384334-Bromo-2-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-1-methoxybenzeneYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-bromo-2-methoxybenzyl alcohol (1.0 g, 4.6 mmol) and imidazole (470 mg, 7.01 mmol) in DMF (15 ml) was added tert-butyldimethylsilyl chloride (1.04 g, 6.91 mmol). The mixture was allowed to stir for 4 h, poured onto water (100 ml) and extracted with ether (3×30 ml). The combined organic phases were washed with water (50 ml), brine (50 ml), dried over sodium sulfate and evaporated under reduced pressure to leave a pale yellow oil. This was purified by chromatography (SiO2, 5% ether/petrol), to give the title compound (1.46 g, 96%) as a colourless oil.

Workup

  1. additionpoured onto water (100 ml)
  2. extractionextracted with ether (3×30 ml)
  3. washThe combined organic phases were washed with water (50 ml), brine (50 ml)
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure
  6. customto leave a pale yellow oil
  7. customThis was purified by chromatography (SiO2, 5% ether/petrol)

Sources & evidence

ORD record
ord-188056945a6047bbba784ee2873b01b0
Source dataset
uspto-grants-2000_08
Patent number
US06110934

Reaction notes

Loading…