Imidazole → 1-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-4-iodobenzene

HRID 341367Notes

Reaction equation

HRID 341367 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[Si:9](Cl)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10].N1C=CN=C1>ClCCl>[C:12]([Si:9]([O:8][C:5]1[CH:6]=[CH:7][C:2]([I:1])=[CH:3][CH:4]=1)([CH3:11])[CH3:10])([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 108944-IodophenolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 148035271-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-4-iodobenzeneYield 95.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Iodophenol (1.0 g, 4.55 mmol) was dissolved in dichloromethane (5 mL). tert-Butyldimethylsilyl chloride (0.685 g, 4.55 mmol) and imidazole (0.309 g, 4.55 mmol) were added. The reaction was stirred overnight at room temperature. The reaction mixture was partitioned between water (30 mL) and dichloromethane (30 mL). The organic layer was removed and the aqueous layer was extracted with dichloromethane (30 mL). The organic layers were combined, dried and concentrated, and the residue was purified by chromatography (0-10% EtOAc/hexanes) to give the title compound as a light yellow oil (1.45 g, 94%).

Workup

  1. customThe reaction mixture was partitioned between water (30 mL) and dichloromethane (30 mL)
  2. customThe organic layer was removed
  3. extractionthe aqueous layer was extracted with dichloromethane (30 mL)
  4. customdried
  5. concentrationconcentrated
  6. customthe residue was purified by chromatography (0-10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-c267bed69794477a91684b8b46a69e9d
Source dataset
uspto-grants-2014_11
Patent number
US08895776B2

Reaction notes

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