Imidazole → 3-(t-Butyldimethylsiloxy)iodobenzene

HRID 2101221

Reaction equation

HRID 2101221 reaction equation
N1C=CN=C1.[I:6][C:7]1[CH:8]=[C:9]([OH:13])[CH:10]=[CH:11][CH:12]=1.[C:14]([Si:18](Cl)([CH3:20])[CH3:19])([CH3:17])([CH3:16])[CH3:15]>ClCCl>[C:14]([Si:18]([O:13][C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([I:6])[CH:8]=1)([CH3:20])[CH3:19])([CH3:17])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 122723-IodophenolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 27572803-(t-Butyldimethylsiloxy)iodobenzeneYield 103.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Imidazole (7.8 g, 115 mmol) was added to a solution of 3-iodophenol (12.7 g, 58 mmol) and tert-butyl(chloro)dimethylsilane (9.9 g, 65 mmol) in dichloromethane (80 mL) at 0° C. The reaction mixture was stirred at rt overnight. The suspension was washed three times with water and once with brine, dried and concentrated to give crude tert-butyl(3-iodophenoxy)dimethylsilane (20 g, 93%).

Workup

  1. washThe suspension was washed three times with water
  2. dry with materialonce with brine, dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-a2e63cdab0da4f35b0ad6064b8d53977
Source dataset
uspto-grants-2009_08
Patent number
US07572817B2

Linked notes

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