Water → (Bromo)(fluorenyl)methane

HRID 841119

Reaktionsgleichung

[C:1]1([C:14](O)=O)[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.OCC1C2CC3C(=CC=CC=3)C=2C=CC=1.P(Br)(Br)[Br:33].O>C1COCC1>[Br:33][CH2:14][C:1]1[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Komponenten

Reaktionsbedingungen

Temperatur: -5 °C

Versuchsvorschrift

Fluorene-1-carboxylic acid was purchased from Aldrich. It was reduced as described in J. Am. Chem. Soc. 1961, 83, 417 via the methyl ester to 1-hydroxymethylfluorene 1H NMR (CDCl3): δ 4.84 ppm (CH2), 3.89 ppm (CH2). 4.1 g (21 mmol) 1-hydroxymethylfluorene dissolved in 60 ml THF was slowly added to 2.54 g PBr3 in 10 ml THF at −5° C. The orange solution was stirred for 1.5 hrs at −5° C. then stirred for 16 hrs at room temperature. This was then poured into iced water, allowed to settle and 5.1 g of 1-bromomethylfluorene was isolated on a frit as an off-white powder. 1H NMR (CDCl3): δ 4.65 ppm (CH2), 3.97 ppm (CH2).

Aufarbeitung

stirringthen stirred for 16 hrs at room temperature

Quellen und Nachweise

ORD-Eintrag: ord-912acc061f8c4dde84f0f9a193a22e84
Quelldatensatz: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06369254B1

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