Imidazole → HCID 57898847, compound

HRID 217280Notes

Reaction equation

HRID 217280 reaction equation
[CH3:1][C:2]([Si:5](Cl)([CH3:7])[CH3:6])([CH3:4])[CH3:3].CN(C)C=O.N1C=CN=C1.[Cl:19][C:20]1[CH:25]=[C:24]([Cl:26])[C:23]([I:27])=[CH:22][C:21]=1[OH:28]>O>[C:2]([Si:5]([O:28][C:21]1[CH:22]=[C:23]([I:27])[C:24]([Cl:26])=[CH:25][C:20]=1[Cl:19])([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:1]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 577494782,4-Dichloro-5-iodophenol

Product 1

HCID 57898847HCID 57898847, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

TBDMSCl (5.22 g) was added to a dimethylformamide solution (50 mL) of imidazole (2.83 g) and 2,4-dichloro-5-iodophenol (10 g), which was synthesized according to the production method described in WO 2001/027088. The mixture was stirred at room temperature for 4 hours. Water (150 mL) was added and extracted with hexane (200 mL). The extract was then washed in succession twice with water (100 mL) and once with brine (100 mL), and was pre-dried over anhydrous sodium sulfate, and then filtered. The solvent was distilled off, and the resulting residue was purified by silica gel column chromatography (developing solvent: hexane) to give tert-butyl-(2,4-dichloro-5-iodophenoxy)-dimethyl-silane as pale yellow oil (11.39 g).

Workup

  1. customwas synthesized
  2. extractionextracted with hexane (200 mL)
  3. washThe extract was then washed in succession twice with water (100 mL) and once with brine (100 mL)
  4. dry with materialwas pre-dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. distillationThe solvent was distilled off
  7. customthe resulting residue was purified by silica gel column chromatography (developing solvent: hexane)

Sources & evidence

ORD record
ord-c5ed7d1aea574fb18e8e501b1be5e2e2
Source dataset
uspto-grants-2012_06
Patent number
US08193351B2

Reaction notes

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