Imidazole → 4-Bromobenzyloxy-tert-butyldimethylsilane

HRID 1468767Notes

Reaction equation

HRID 1468767 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.N1C=CN=C1.[C:15]([Si:19]([CH3:22])([CH3:21])Cl)([CH3:18])([CH3:17])[CH3:16].O>CN(C)C=O>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][O:7][Si:19]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:22])[CH3:21])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 701194-Bromobenzyl alcohol

Product 1

HCID 108595834-Bromobenzyloxy-tert-butyldimethylsilaneYield 95.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 4-bromobenzyl alcohol (18.0 g, 96.2 mmol) and imidazole (7.86 g, 115 mmol) in N,N-dimethylformamide (200 ml) was added tert-butyl dimethylchlorosilane (17.4 g, 115 mmol) at room temperature. The mixture was stirred for 5 hours. The mixture was poured into water, and extracted with ethyl acetate. The organic layer was washed with water (three times), dried over sodium sulfate, and concentrated in vacuo. The residue was purified by silica gel column chromatography (eluent; hexane/ethyl acetate=95/5) to afford (4-bromobenzyloxy) (tert-butyl)dimethylsilane as a colorless oil (27.7 g, 91.8 mmol, 92%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water (three times)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography (eluent; hexane/ethyl acetate=95/5)

Sources & evidence

ORD record
ord-530823fd3722422cb924f8c67b8b1f69
Source dataset
uspto-grants-2015_04
Patent number
US09006232B2

Reaction notes

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