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

HRID 1846033Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1846033
[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]

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 73012-MethyltetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-36c66526bb2746d2a044d3adb874ff5b
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08952008B2

Notizen zur Reaktion

Wird geladen…