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4-Bromostyrene → Diphenylphosphinostyrene

HRID 729214
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 729214
[C:1]1([C:7]#[C:8]C#C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Mg].BrC1C=CC(C=C)=CC=1.Cl[P:22]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1COCC1>[CH:7]([C:1]1[CH:2]=[CH:3][C:4]([P:22]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:5][CH:6]=1)=[CH2:8]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 162634-BromostyreneHCID 66180ChlorodiphenylphosphineHCID 5462224MagnesiumHCID 11355482Buta-1,3-diynylbenzene

Produkt 1

HCID 11437688Diphenylphosphinostyrene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel
3×

Versuchsvorschrift

Polymerizable Gold Complex (3-1) was synthesized by reacting the gold complex obtained by the reaction between sodium tetrachloroaurate (III) and triphenylphosphine having a polymerizable functional group, with phenylbutadiyne synthesized by a known method (see, P. Cadiot and W. Chodkiewicz, Chemistry of Acetylenes, H. G. Viehe, ed., Marcel Dekker, New York (1969)). More specifically, 20 ml of dried THF was added to 341 mg (14 mmol) of magnesium and thereto, a 10 ml THF solution containing 2.70 g (15 mmol) of 4-bromostyrene was added dropwise to prepare a Grignard reagent. To the resulting solution, a 10 ml THF solution containing 2.50 g (11 mmol) of chlorodiphenylphosphine was added dropwise and stirred at room temperature of 1.5 hours. After removing the solvent by distillation under reduced pressure, the residue was purified by silica gel column chromatography and recrystallized from a hexane solution to obtain 2.30 g (8.3 mmol) of (4-vinylphenyl)diphenylphosphine Compound (B).

Aufarbeitung

  1. additionwas added dropwise
  2. additionwas added dropwise
  3. customAfter removing the solvent
  4. distillationby distillation under reduced pressure
  5. customthe residue was purified by silica gel column chromatography
  6. customrecrystallized from a hexane solution

Quellen und Nachweise

ORD-Eintrag
ord-223775f6a560431b879c384c695c6fee
Quelldatensatz
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07582363B2

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