5-Bromo-1,2,3-trimethoxybenzene → (5-Methoxy-2-nitro-phenyl)-(3,4,5-trimethoxy-phenyl)-methanol

HRID 970994Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 970994
COC1C=CC(C(C2C=CC(OC)=C(OC)C=2)O)=CC=1[N+]([O-])=O.[CH3:24][O:25][C:26]1[CH:27]=[C:28](Br)[CH:29]=[C:30]([O:34][CH3:35])[C:31]=1[O:32][CH3:33].[Mg].[CH3:38][O:39][C:40]1[CH:41]=[CH:42][C:43]([N+:48]([O-:50])=[O:49])=[C:44]([CH:47]=1)[CH:45]=[O:46]>>[CH3:38][O:39][C:40]1[CH:41]=[CH:42][C:43]([N+:48]([O-:50])=[O:49])=[C:44]([CH:45]([C:28]2[CH:27]=[C:26]([O:25][CH3:24])[C:31]([O:32][CH3:33])=[C:30]([O:34][CH3:35])[CH:29]=2)[OH:46])[CH:47]=1

Komponenten

5

Edukt 4

HCID 758855-Bromo-1,2,3-trimethoxybenzeneHCID 2303715-Methoxy-2-nitrobenzaldehydeHCID 5462224MagnesiumHCID 69204044(4-Methoxy-3-nitro-phenyl)-(3,4-dimethoxy-phenyl)-methanol

Produkt 1

HCID 11783038(5-Methoxy-2-nitro-phenyl)-(3,4,5-trimethoxy-phenyl)-methanolAusbeute 53,6 %

Versuchsvorschrift

(5-Methoxy-2-nitro-phenyl)-(3,4,5-trimethoxy-phenyl)-methanol was prepared analogously to (4-methoxy-3-nitro-phenyl)-(3,4-dimethoxy-phenyl)-methanol using 3,4,5-trimethoxy-bromobenzene (4.6 g, 18.5 mmol), magnesium turning (0.5 g, 18.5 mmol) and 5-methoxy-2-nitro-benzaldehyde (2.8 g, 15.5 mmol). The crude product was purified by flash chromatography (silica gel, CH2Cl2:EtOAc 9:1) to afford (5-methoxy-2-nitro-phenyl)-(3,4,5-trimethoxy-phenyl)-methanol (2.9 g, 53%); 1H NMR (CDCl3) δ 8.08 (d, J=9 Hz, 1H), 7.20 (d, J=2 Hz, 1H), 6.91-6.87 (dd, J=3, 9 Hz, 1H), 6.57 (s, 2H), 6.45 (d, J=4 Hz, 1H), 3.88 (s, 3H), 3.82 (s, 3H), 3.80 (s, 6H), 3.04 (d, J=4 Hz, 1H).

Aufarbeitung

  1. customThe crude product was purified by flash chromatography (silica gel, CH2Cl2:EtOAc 9:1)

Quellen und Nachweise

ORD-Eintrag
ord-d604d006bdb2435380b296217de17999
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07312241B2

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