Imidazole → 2-[5-Bromo-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)phenyl]propan-2-ol

HRID 1626830Notes

Reaction equation

HRID 1626830 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:12][OH:13])=[C:6]([C:8]([OH:11])([CH3:10])[CH3:9])[CH:7]=1.N1C=CN=C1.[C:19]([Si:23]([CH3:26])([CH3:25])Cl)([CH3:22])([CH3:21])[CH3:20].O>CN(C)C=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:12][O:13][Si:23]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:26])[CH3:25])=[C:6]([C:8]([OH:11])([CH3:10])[CH3:9])[CH:7]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 578036042-(5-Bromo-2-(hydroxymethyl)phenyl)propan-2-ol

Product 1

HCID 681932522-[5-Bromo-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)phenyl]propan-2-olYield 70.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-[5-Bromo-2-(hydroxymethyl)phenyl]propan-2-ol (1.1 g, 4.4 mmol) and imidazole (0.78 g, 12 mmol) were dissolved in N,N-dimethylformamide (5 mL), and tert-butyldimethylchlorosilane (0.86 g, 5.7 mmol) was added, followed by stirring at room temperature overnight. Water was added to the reaction solution, followed by extraction with hexane, and subsequently the extract was washed sequentially with water and a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. After the organic layer was concentrated under reduced pressure, the resulting residue was purified by chromatography on a silica gel column (Biotage Ltd., elution solvent: hexane/ethyl acetate) to afford the title compound (1.1 g, 3.1 mmol) as a colorless oil (yield 70%).

Workup

  1. extractionfollowed by extraction with hexane
  2. washsubsequently the extract was washed sequentially with water
  3. dry with materiala saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate
  4. concentrationAfter the organic layer was concentrated under reduced pressure
  5. customthe resulting residue was purified by chromatography on a silica gel column (Biotage Ltd., elution solvent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-d9c010c88d3349d3957be1435b40a0aa
Source dataset
uspto-grants-2014_07
Patent number
US08785462B2

Reaction notes

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