Iodine → 4-Iodo-1-(methyldiisopropyloxysilyl)benzene

HRID 1836929Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1836929
Br[C:2]1[CH:7]=[CH:6][C:5]([Si:8]([CH3:17])([O:13][CH:14]([CH3:16])[CH3:15])[O:9][CH:10]([CH3:12])[CH3:11])=[CH:4][CH:3]=1.[Mg].[I:19]I>C1COCC1>[I:19][C:2]1[CH:7]=[CH:6][C:5]([Si:8]([CH3:17])([O:13][CH:14]([CH3:16])[CH3:15])[O:9][CH:10]([CH3:12])[CH3:11])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 807IodineHCID 5462224MagnesiumHCID 120405694-Bromo1-(methyldiisopropyloxysilyl)benzene2×

Produkt 1

HCID 120405754-Iodo-1-(methyldiisopropyloxysilyl)benzeneAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

A solution of 4-bromo-1-(methyldiisopropyloxysilyl)benzene (13.35 g, 42.1 mmol) in THF (85 ml) was added slowly dropwise at 0° C. to a suspension of magnesium chips (1.53 g, 63.1 mmol) in THF (10 ml). After one hour, the Grignard reagent of 4-bromo-1-(methyldiisopropyloxysilyl)benzene was added dropwise at 0° C. to iodine (13.87 g, 54 mmol) dissolved in 50 ml of dry THF. After stirring during four hours, the solvent was pumped off and the residue was extracted with dry pentane (200 ml) and filtered. The yellow solution was concentrated to afford 4-iodo-1-(methyldiisopropyloxysilyl)benzene as a yellow oil of in 84% yield. 1H NMR (CDCl3, δ, ppm) 7.76 (2H, d); 7.42 (2H, d); 4.21 (2H, heptuplet); 1.23 (12H, t); 0.37 (3H, s).

Aufarbeitung

  1. extractionthe residue was extracted with dry pentane (200 ml)
  2. filtrationfiltered
  3. concentrationThe yellow solution was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-4fa1edfa5aff4892a6f8d1fc41fa868c
Quelldatensatz
uspto-grants-2004_08
Patentnummer
US06780471B2

Notizen zur Reaktion

Wird geladen…