Imidazole → [(3-Bromo-5-fluorobenzyl)oxy](tert-butyl)diphenylsilane

HRID 1012024Notes

Reaction equation

HRID 1012024 reaction equation
N1C=CN=C1.[C:6]([Si:10]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)Cl)([CH3:9])([CH3:8])[CH3:7].[Br:24][C:25]1[CH:26]=[C:27]([CH2:32][OH:33])[CH:28]=[C:29]([F:31])[CH:30]=1.O>CN(C)C=O>[Br:24][C:25]1[CH:26]=[C:27]([CH:28]=[C:29]([F:31])[CH:30]=1)[CH2:32][O:33][Si:10]([C:6]([CH3:9])([CH3:8])[CH3:7])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 94078tert-ButyldiphenylchlorosilaneHCID 2769402(3-Bromo-5-fluorophenyl)methanol

Product 1

HCID 58843476[(3-Bromo-5-fluorobenzyl)oxy](tert-butyl)diphenylsilaneYield 87.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Imidazole (3.3 g) and tert-butyl-diphenylchlorosilane (10.0 g) were added to a solution of (3-bromo-5-fluorophenyl)methanol (5.0 g) in dimethylformamide (50 ml), and the mixture was stirred over night at room temperature. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated saline solution and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated from the filtrate under reduced pressure to give the residue. The resulting residue was purified by silica gel column chromatography (n-hexane-ethyl acetate) to obtain [(3-bromo-5-fluorobenzyl)oxy] (tert-butyl)diphenylsilane (9.5 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated saline solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationAfter filtration
  5. customthe solvent was evaporated from the filtrate under reduced pressure
  6. customto give the residue
  7. customThe resulting residue was purified by silica gel column chromatography (n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-6fbd98208e6a48cf9dc270489f557727
Source dataset
uspto-grants-2011_07
Patent number
US07977466B2

Reaction notes

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