Imidazole → tert-Butyl(4-chloro-3-iodophenoxy)dimethylsilane

HRID 1846033Notes

Reaction equation

HRID 1846033 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[I:9].[Si:10](Cl)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11].N1C=CN=C1.CCOC(C)=O>CC1CCCO1>[C:13]([Si:10]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([I:9])[CH:4]=1)([CH3:12])[CH3:11])([CH3:16])([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 8857Ethyl AcetateHCID 28928tert-Butyldimethylsilyl chlorideHCID 229287294-Chloro-3-iodophenol

Product 1

HCID 86723256tert-Butyl(4-chloro-3-iodophenoxy)dimethylsilaneYield 30%

Reagents, catalysts & solvents 1

HCID 73012-MethyltetrahydrofuranSolvent

Procedure

To a solution of 4-chloro-3-iodophenol (2 g. 7.86 mmol) in anhydrous 2-methyltetrahydrofuran (10 mL) was added tert-butyldimethylsilyl chloride (1.25 g, 8.28 mmol) followed by imidazole (642 mg, 68.1 mmol) The resulting mixture was stirred at room temperature for 3 hours. EtOAc (10 mL) was added and the mixture washed with aqueous sodium hydroxide solution (2M, 3×10 mL), water (10 mL), and brine (10 mL), dried over Na2SO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with heptane:EtOAc 90:10 to afford the title compound as colourless oil in 30% yield, 870 mg.

Workup

  1. washthe mixture washed with aqueous sodium hydroxide solution (2M, 3×10 mL), water (10 mL), and brine (10 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel column chromatography
  5. washeluting with heptane:EtOAc 90:10

Sources & evidence

ORD record
ord-36c66526bb2746d2a044d3adb874ff5b
Source dataset
uspto-grants-2015_02
Patent number
US08952008B2

Reaction notes

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