methyl 4-(4-bromo-2-nitrophenyl)tetrahydro-2H-pyran-4-carboxylate → 6-Bromo-1,2-dihydrospiro[indole-3,4'-oxane]-2-one
Reaktionsgleichung
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:14](OC)=[O:15])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[C:4]([N+:18]([O-])=O)[CH:3]=1>[Fe].CC(O)=O>[Br:1][C:2]1[CH:3]=[C:4]2[NH:18][C:14](=[O:15])[C:8]3([CH2:13][CH2:12][O:11][CH2:10][CH2:9]3)[C:5]2=[CH:6][CH:7]=1Komponenten
4
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 100 °C
Versuchsvorschrift
Prepared according to procedure J using methyl 4-(4-bromo-2-nitrophenyl)tetrahydro-2H-pyran-4-carboxylate (6.67 g, 19.4 mmol), AcOH (97 mL) and Fe powder (5.42 g, 96.97 mmol) and heating the mixture at 100° C. for 2 h. After purification 6-bromo-2′,3′,5′,6′-tetrahydrospiro[indoline-3,4′-pyran]-2-one was obtained as an orange solid. Mass Spectrum (ESI) m/e=282 [(M+1) (79Br)] and 284 [(M+1) (81Br)].