Imidazole → (2-Bromobenzyloxy)tert-butyldimethylsilane

HRID 1349450Notes

Reaction equation

HRID 1349450 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].N1C=CN=C1.[C:15]([Si:19]([CH3:22])([CH3:21])Cl)([CH3:18])([CH3:17])[CH3:16].C(=O)([O-])O.[Na+]>CN(C)C=O>[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][O:5][Si:19]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:22])[CH3:21]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 728502-Bromobenzyl alcoholHCID 516892Sodium Bicarbonate

Product 1

HCID 13424900(2-Bromobenzyloxy)tert-butyldimethylsilaneYield 101.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Bromobenzyl alcohol (25.0 g) was dissolved in N,N-dimethylformamide (150 ml) and imidazole (20.0 g) and tert-butyldimethylchlorosilane (22.2 g) were added. The reaction mixture was stirred at room temperature for 2 hr. The reaction mixture was poured into 5% aqueous sodium hydrogencarbonate solution and extracted with ethyl acetate. The organic layer was washed successively with 5% aqueous sodium hydrogencarbonate solution, water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the title compound (40.9 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed successively with 5% aqueous sodium hydrogencarbonate solution, water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0c0db916e9344db2a6abf66e9329944d
Source dataset
uspto-grants-2007_05
Patent number
US07211685B2

Reaction notes

Loading…