Toluene → Pentafluorobenzyltriphenylphosphonium bromide

HRID 464124

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-1e46d549e2f34f48b3a86a51324c3fb5
Quelldatensatz: uspto-grants-1985_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04546184

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