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

HRID 1007469Notes

Reaction equation

HRID 1007469 reaction equation
N1C=CN=C1.[C:6]([Si:10](Cl)([CH3:12])[CH3:11])([CH3:9])([CH3:8])[CH3:7].[I:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1.O>CN(C)C=O>[I:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][Si:10]([CH3:12])([CH3:11])[C:6]([CH3:9])([CH3:8])[CH3:7])=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 108944-IodophenolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 148035271-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-4-iodobenzeneYield 83.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

387 mg of imidazole and 411 mg of tertbutyldimethylsilyl chloride is added at ambient temperature and under an inert atmosphere to 500 mg of para-iodo-phenol in 4 ml of dimethylformamide and the mixture is maintained under agitation for 15 hours at ambient temperature then for 1 hour at 40° C. The reaction medium is poured into water, and the aqueous phase is extracted with dichloromethane. The organic phase is then dried and evaporated under reduced pressure. In this way 636 mg of expected product is obtained.

Workup

  1. extractionthe aqueous phase is extracted with dichloromethane
  2. customThe organic phase is then dried
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-d3479562a4a14563befda52f392584ff
Source dataset
uspto-grants-2004_09
Patent number
US06794415B2

Reaction notes

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