1-Naphthalenamine, 5-nitro- → 1-Fluoro-5-nitronaphthalene

HRID 880471

Reaktionsgleichung

N([O-])=O.[Na+].[N+:5]([C:8]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:9]=1[CH:10]=[CH:11][CH:12]=[C:13]2N)([O-:7])=[O:6].[F:19][P-](F)(F)(F)(F)F.[H+]>O>[F:19][C:13]1[C:14]2[C:9](=[C:8]([N+:5]([O-:7])=[O:6])[CH:17]=[CH:16][CH:15]=2)[CH:10]=[CH:11][CH:12]=1

Komponenten

Reaktionsbedingungen

Temperatur: -5 °C

Versuchsvorschrift

Sodium nitrite (660 mg, 9.57 mmol) was added portionwise to a suspension of 5-nitronaphthalen-1-amine (1.2 g, 6.38 mmol) in a 1:1 mixture of water/concentrated hydrochloric acid (10 mL) at −5° C. The mixture was stirred for 15 min at −5° C. and a 60% w/w hexafluoro phosphoric acid solution (6 mL) was added. The brown precipitate was filtered and washed with cold water and diethyl ether and then allowed to dry in vacuo. The resulting solid was suspended in toluene and heated to 110° C. for 2 h before the mixture was then allowed to cool to ambient temperature and the solvent removed in vacuo to afford the crude product. Purification by column chromatography over silica gel (100-200 mesh) using petroleum ether as eluent afforded 1-fluoro-5-nitro-naphthalene (450 mg, 37%) as a yellow solid.

Aufarbeitung

filtrationThe brown precipitate was filtered
washwashed with cold water and diethyl ether
customto dry in vacuo
temperatureheated to 110° C. for 2 h before the mixture
temperatureto cool to ambient temperature
customthe solvent removed in vacuo
customto afford the crude product
customPurification by column chromatography over silica gel (100-200 mesh)

Quellen und Nachweise

ORD-Eintrag: ord-e7c74a2612ca4b13a40f0adf05f393d4
Quelldatensatz: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08993574B2

Verknüpfte Notizen

Wird geladen…