Toluene → Pentafluorobenzyltriphenylphosphonium bromide

HRID 1249649

Reaktionsgleichung

C1([P:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)C=CC=CC=1.[F:20][C:21]1[C:26](C[Br:28])=[C:25]([F:29])[C:24]([F:30])=[C:23]([F:31])[C:22]=1[F:32].[C:33]1([CH3:39])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>>[Br-:28].[F:29][C:25]1[C:26]([P+:7]([CH2:39][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[C:21]([F:20])[C:22]([F:32])=[C:23]([F:31])[C:24]=1[F:30]

Komponenten

Edukt 3

HCID 1140Toluene

HCID 11776Triphenylphosphine

HCID 74484Pentafluorobenzyl bromide

Produkt 1

HCID 87730649Pentafluorobenzyltriphenylphosphonium bromideAusbeute 90 %

Versuchsvorschrift

A five-liter, three-necked flask equipped with a mechanical stirrer, reflux condenser, and thermometer was charged with toluene (3.3 liters), triphenylphosphine (686 g, 2.62 mole), and pentafluorobenzyl bromide (343 g, 1.31 mole). The contents were stirred and heated slowly to reflux. A white precipitate formed as the reaction progressed. At the completion of the reaction the flask was cooled to ambient temperature and the solid product was filtered and washed with hot toluene (2.6 liters). These solids were dried in a vacuum desiccator to give a 90% yield of pentafluorobenzyltriphenylphosphonium bromide.

Aufarbeitung

customA five-liter, three-necked flask equipped with a mechanical stirrer
temperaturereflux condenser
temperatureheated slowly
temperatureto reflux
customA white precipitate formed as the reaction
customAt the completion of the reaction the flask
filtrationthe solid product was filtered
washwashed with hot toluene (2.6 liters)
customThese solids were dried in a vacuum desiccator

Quellen und Nachweise

ORD-Eintrag: ord-17688f8e310142d09b1573f1989d69f4
Quelldatensatz: uspto-grants-1986_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04633020

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