N-bromobutanimide → 2-Bromo-1-[6-(difluoromethoxy)pyridin-3-yl]ethan-1-one
Reaktionsgleichung
C([O:5][C:6]([C:8]1[CH:9]=[CH:10][C:11]([O:14][CH:15]([F:17])[F:16])=[N:12][CH:13]=1)=[CH2:7])CCC.[Br:18]N1C(=O)CCC1=O>C1COCC1.O.O>[Br:18][CH2:5][C:6]([C:8]1[CH:13]=[N:12][C:11]([O:14][CH:15]([F:17])[F:16])=[CH:10][CH:9]=1)=[O:7]Komponenten
5
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
A solution of 100 mg (0.41 mmol) of 5-(1-butoxyvinyl)-2-difluoromethoxypyridine in 4 mL of THF/H2O (3/1: v/v) is cooled to 0° C. 74 mg (0.41 mmol) of N-bromosuccinimide are then added in a single portion. The yellow solution is stirred at 0° C. for 1 hour and then taken up in water and extracted with EtOAc. The organic phase is washed with saturated aqueous NaHCO3 solution and then with saturated NaCl solution, dried over magnesium sulfate and then evaporated to dryness. The crude product is purified by chromatography on silica gel (eluent: 20/80 EtOAc/heptane to 40/60 EtOAc/heptane over 15 minutes) to give 82 mg of 2-bromo-1-(6-difluoromethoxypyrid-3-yl)ethanone, corresponding to the following characteristics:
Aufarbeitung
- extractionextracted with EtOAc
- washThe organic phase is washed with saturated aqueous NaHCO3 solution
- dry with materialwith saturated NaCl solution, dried over magnesium sulfate
- customevaporated to dryness
- customThe crude product is purified by chromatography on silica gel (eluent: 20/80 EtOAc/heptane to 40/60 EtOAc/heptane over 15 minutes)
Quellen und Nachweise
- ORD-Eintrag
- ord-f36da45fcf604d4fb0169556ec4d7c5b
- Quelldatensatz
- uspto-grants-2016_04
- Patentnummer
- US09321790B2
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