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Methoxymethyl-triphenylphosphonium chloride → 2,6-Diisopropyl-4-bromo-beta-methoxystyrene

HRID 1097162
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1097162
[Cl-].[CH3:2][O:3][CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[CH:34]([C:37]1[CH:44]=[C:43]([Br:45])[CH:42]=[C:41]([CH:46]([CH3:48])[CH3:47])[C:38]=1[CH:39]=O)([CH3:36])[CH3:35]>C1COCC1>[CH:34]([C:37]1[CH:44]=[C:43]([Br:45])[CH:42]=[C:41]([CH:46]([CH3:48])[CH3:47])[C:38]=1[CH:39]=[CH:2][O:3][CH3:4])([CH3:36])[CH3:35]
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Komponenten

5

Edukt 3

HCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 2733832Lithium HexamethyldisilazideHCID 574376682,6-Diisopropyl-4-bromobenzaldehyde

Produkt 1

HCID 668135662,6-Diisopropyl-4-bromo-beta-methoxystyreneAusbeute 78,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028Tetrahydrofuran
Lösungsmittel
2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Methoxymethyl triphenylphosphonium chloride (18.68 g, 54.5 mmol) was suspended in 200 mL of THF at −78° C. Lithium hexamethyldisilazide (1.0 M in THF, 50 mL) was added dropwise. The resulting mixture was warmed up to 0° C. with stirring. After cooling the solution to −78° C., 2,6-diisopropyl-4-bromobenzaldehyde (11.5 g, 42.7 mmol) in 20 mL of THF was added dropwise. The mixture was slowly warmed up to room temperature and continually stirred overnight. After regular work up, the crude product was distilled at 165° C. under vacuum to afford 2,6-diisopropyl-4-bromo-β-methoxystyrene (10 g). This product was dissolved in 20 mL of dioxane and 100 mL of 18% HCl solution and refluxed at 100° C. for 6 h. After regular work up, the crude product was distilled at 160° C. under vacuum to afford 2,6-diisopropyl-4-bromophenylacetaldehyde (7.5 g).

Aufarbeitung

  1. temperatureAfter cooling the solution to −78° C.
  2. temperatureThe mixture was slowly warmed up to room temperature and continually stirred overnight
  3. distillationAfter regular work up, the crude product was distilled at 165° C. under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-dc1fb97c62564a1981166e83b631945f
Quelldatensatz
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08142909B2

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