Imidazole → 1-Bromo-3-((((1,1-dimethylethyl)dimethylsilyl)oxy)methyl)benzene

HRID 1838857Notes

Reaction equation

HRID 1838857 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6].N1C=CN=C1.[Si:15](Cl)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16].O>CN(C)C=O>[Si:15]([O:6][CH2:5][C:4]1[CH:3]=[C:2]([Br:1])[CH:9]=[CH:8][CH:7]=1)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 851413-Bromobenzyl alcohol

Product 1

HCID 220331471-Bromo-3-((((1,1-dimethylethyl)dimethylsilyl)oxy)methyl)benzeneYield 99.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-bromobenzylalcohol (18.7 g) in dimethylformamide (100 ml) was added imidazole (13.6 g) and t-butyidimethylsilylchloride (15.8 g). The mixture was stirred for 2 hours at room temperature. The reaction mixture was poured into water (300 ml) and then extracted with a mixture of hexane and ethyl acetate (1:1, 100 ml×2). The extract was washed with 0.5N hydrochloric acid, water and a saturated aqueous solution of sodium chloride, successively, dried over anhyrous sodium sulfate and concentrated to give the title compound (30.1 g) having the following physical data.

Workup

  1. extractionextracted with a mixture of hexane and ethyl acetate (1:1, 100 ml×2)
  2. washThe extract was washed with 0.5N hydrochloric acid, water
  3. dry with materiala saturated aqueous solution of sodium chloride, successively, dried over anhyrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c73e94e5c69a43a8b95dbcec9180d1d5
Source dataset
uspto-grants-2004_01
Patent number
US06677333B1

Reaction notes

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