Reaktionsgleichung
[Al](Br)(Br)Br.[CH:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[OH:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:21]=1[N:20]=[CH:19][CH:18]=[CH:17]2.Br.Cl>>[C:5]1([CH:14]2[CH2:13][C:12](=[O:11])[C:21]3[N:20]=[CH:19][CH:18]=[CH:17][C:16]=3[CH2:15]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1Komponenten
Reaktionsbedingungen
- Temperatur
- 40 °C
Versuchsvorschrift
To a stirred suspension of AlBr3 (4.80 g, 18 mmol) in benzene (4.8 mL, 55 mmol) was added 8-hydroxyquinoline (0.50 g, 3.4 mmol). The resulting mixture was saturated with HBr (g) and then stirred at 40° C. for 48 h. The reaction mixture was cooled to ambient temperature and poured onto ice (50 g). The resulting mixture was adjusted to pH=1-2 by addition of concentrated HCl and then was extracted with EtOAc (3×20 mL), discarding the organic extracts. The aqueous layer was adjusted to pH 12 by addition of NaOH (s), keeping the temperature below 10° C., and was then extracted with EtOAc (3×20 mL). These combined organic extracts were washed with brine (30 mL), dried over sodium sulfate, filtered, and concentrated in vacuo to give the title compound in sufficient purity for use in the next step. MS: m/z=223.8 (M+1).
Aufarbeitung
- temperatureThe reaction mixture was cooled to ambient temperature
- additionpoured onto ice (50 g)
- extractionwas extracted with EtOAc (3×20 mL)
- additionThe aqueous layer was adjusted to pH 12 by addition of NaOH (s)
- customthe temperature below 10° C.
- extractionwas then extracted with EtOAc (3×20 mL)
- washThese combined organic extracts were washed with brine (30 mL)
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-c51cf7a87f24409c9eca2cbe59d0345b
- Quelldatensatz
- uspto-grants-2016_01
- Patentnummer
- US09227973B2
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