Water → HCID 66999466, Verbindung

HRID 558080

Reaktionsgleichung

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[CH:9][C:10]2[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][C:11]=2[OH:17])=[C:4](F)[CH:3]=1.C([O-])([O-])=O.[K+].[K+].O>CS(C)=O.C1OCCOCCOCCOCCOCCOC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[N:8]=[CH:9][C:10]3[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][C:11]=3[O:17][C:4]=2[CH:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 140 °C

Versuchsvorschrift

To a solution of 2-[(4-bromo-2-fluorophenyl)iminomethyl]-3-methylphenol (31.7 g, 102.9 mmol) in DMSO (0.27 L), K2CO3 (28.6 g, 206.9 mmol) and 18-Crown-6 (477 mg, 1.8 mmol) were added. The resulting mixture was stirred at 140° C. for 1 h and then allowed to cool to ambient temperature. Water was added and the mixture was extracted with toluene/ethyl acetate (8:2). The combined organic layers were washed with water and with brine, dried (Na2SO4) and evaporated to afford the crude compound which was purified by flash chromatography (SiO2, CH2Cl2) to give 7-bromo-1-methyldibenz[b,f][1,4]oxazepine (25.05 g, 84%). 1H-NMR (400 MHz, CDCl3) δ 2.47 (s, 3H), 7.01 (m, 2H), 7.18-7.37 (m, 4H), 8.77 (s, 1H). (m/z)=288+290 (M+H)+.

Aufarbeitung

temperatureto cool to ambient temperature
extractionthe mixture was extracted with toluene/ethyl acetate (8:2)
washThe combined organic layers were washed with water and with brine
dry with materialdried (Na2SO4)
customevaporated
customto afford the crude compound which
customwas purified by flash chromatography (SiO2, CH2Cl2)

Quellen und Nachweise

ORD-Eintrag: ord-11c3e41af9b4423fbf771a2135a8bfc0
Quelldatensatz: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08063037B2

Verknüpfte Notizen

Wird geladen…