Reaktionsgleichung
[Br-:1].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.[CH2:34]([O:41][C:42]1[CH:47]=[C:46]([F:48])[CH:45]=[CH:44][C:43]=1[C:49](=[O:51])[CH3:50])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.CCCCCC.CCOC(C)=O>C1COCC1.O>[CH2:34]([O:41][C:42]1[CH:47]=[C:46]([F:48])[CH:45]=[CH:44][C:43]=1[C:49](=[O:51])[CH2:50][Br:1])[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
Phenyltrimethylammonium tribromide (1.55 g, 4.13 mmol) was added to a solution of 2′-(benzyloxy)-4′-fluoroacetophenone (1.01 g, 4.13 mmol) in THF (10 mL), and the mixture stirred at room temperature for 45 minutes, over which time the orange solution faded and a white precipitate formed. Tlc analysis (9:1 hexane:EtOAc) showed the reaction to be complete. The mixture was poured into water (20 mL) and extracted with ether (2×50 mL). The combined ethereal extracts were dried (MgSO4) and the solvents removed in vacuo to give crude 2′-(benzyloxy)-2-bromo-4′-fluoroacetophenone as a colourless oil, which was used in the following step without purification. Rf 0.47 (9:1 hexane:EtOAc); δH (CDCl3) 7.89 (1H, dd, J=9.4 and 6.9 Hz), 7.45-7.40 (5H, m), 6.77-6.74 (2H, m), 5.15 (2H, s), 4.47 (2H, s); LCMS retention time 2.75 min, M+H+ 323.3/325.3.
Aufarbeitung
- customa white precipitate formed
- customthe reaction
- extractionextracted with ether (2×50 mL)
- dry with materialThe combined ethereal extracts were dried (MgSO4)
- customthe solvents removed in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-28edf7b8c982425194a1a147a8623822
- Quelldatensatz
- uspto-grants-2009_11
- Patentnummer
- US07612201B2
Verknüpfte Notizen
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