Phenyltrimethylammonium bromide dibromide → N-[3-benzyloxy-4-(2,2-dibromo-acetyl)phenyl]-acetamide
Reaktionsgleichung
[Br-:1].[Br-:2].[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.[C:34]([C:37]1[CH:42]=[CH:41][C:40]([NH:43][C:44](=[O:46])[CH3:45])=[CH:39][C:38]=1[O:47][CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)(=[O:36])[CH3:35]>C1COCC1>[CH2:48]([O:47][C:38]1[CH:39]=[C:40]([NH:43][C:44](=[O:46])[CH3:45])[CH:41]=[CH:42][C:37]=1[C:34](=[O:36])[CH:35]([Br:2])[Br:1])[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
Phenyltrimethylammonium tribromide (102 mg, 0.272 mmol) was added to a solution of N-(4-acetyl-3-benzyloxy-phenyl)-acetamide (35 mg, 0.124 mmol) in THF (3.5 mL), and stirred at room temperature for 2 hours. The mixture was partitioned between water (25 mL) and EtOAc (25 mL), the layers separated and the organic layer dried (MgSO4). The solvents were removed in vacuo to give crude N-[3-benzyloxy-4-(2,2-dibromo-acetyl)-phenyl]-acetamide (54 mg, 100%) as a pale brown solid; δH (CDCl3) 7.92 (1H, br s), 7.85 (1H, d, J=8.5 Hz), 7.55 (1H, br s), 7.50-7.35 (5H, m), 7.09 (1H, s), 6.78 (1H, dd, J=8.5, 1.9 Hz), 5.20 (2H, s), 2.21 (3H, s); LCMS retention time 2.65 min, M+H+ 440.1/442.1/444.1. The mixture was used crude in the next step.
Aufarbeitung
- customThe mixture was partitioned between water (25 mL) and EtOAc (25 mL)
- customthe layers separated
- dry with materialthe organic layer dried (MgSO4)
- customThe solvents were removed in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-250d864f162b4a98bbf6901e7f22625f
- Quelldatensatz
- uspto-grants-2009_11
- Patentnummer
- US07612201B2
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