1,4-Dibromobenzene → 4-Bromo1-(methyldiisopropyloxysilyl)benzene

HRID 1836928Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1836928
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Mg]Br)=[CH:4][CH:3]=1.Cl[CH2:11][SiH:12]([O:17][CH:18]([CH3:20])[CH3:19])[O:13][CH:14]([CH3:16])[CH3:15].BrC1C=CC(Br)=CC=1>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Si:12]([CH3:11])([O:17][CH:18]([CH3:20])[CH3:19])[O:13][CH:14]([CH3:16])[CH3:15])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 78041,4-DibromobenzeneHCID 123979138ChloromethyldiisopropyloxysilaneHCID 178419617HCID 178419617, Verbindung

Produkt 1

HCID 120405694-Bromo1-(methyldiisopropyloxysilyl)benzeneAusbeute 33 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 4-bromophenyl magnesium bromide (7.82 g, 50 mmol) in THF (100 ml) was added at 0° C. to a solution of chloromethyldiisopropyloxysilane (10 g, 48 mmol). The mixture was stirred at room temperature for 24 hours. After evaporation of the solvent, the yellow solid was extracted by 200 ml of dry pentane and filtered. The solvent was then pumped off to afford a yellow oil. Residual 1,4-dibromobenzene was sublimated under vacuum at 80° C. to give 4-bromo-1-(methyldiisopropyloxysilyl)benzene as a colourless oil in 33% yield (5.1 g, 16 mmol). 1H NMR (CDCl3, δ, ppm) 7.52 (4H, m); 4.22 (2H, heptuplet); 1.24 (12H, d); 0.39 (3H, s). 13C NMR (CDCl3, δ, ppm) 136.1, 134.5, 131.3, 125.1, 65.8, 26.1, −2.8. 29Si NMR (CDCl3, δ, ppm) −21.8.

Aufarbeitung

  1. customAfter evaporation of the solvent
  2. extractionthe yellow solid was extracted by 200 ml of dry pentane
  3. filtrationfiltered
  4. customto afford a yellow oil
  5. customwas sublimated under vacuum at 80° C.

Quellen und Nachweise

ORD-Eintrag
ord-1f7faa09f72c4f89bf3b147359b0fa55
Quelldatensatz
uspto-grants-2004_08
Patentnummer
US06780471B2

Notizen zur Reaktion

Wird geladen…