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

HRID 2378209Notes

Reaction equation

HRID 2378209 reaction equation
COC1C=CC([CH:9]([C:11]2[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[C:13]([O:21][CH3:22])[CH:12]=2)[OH:10])=CC=1[N+]([O-])=O.COC1C=C(Br)C=C(OC)C=1OC.[Mg].[CH3:40][O:41][C:42]1[CH:43]=[C:44]([CH:47]=[CH:48][C:49]=1[N+:50]([O-:52])=[O:51])C=O>>[CH3:40][O:41][C:42]1[CH:43]=[C:44]([CH:9]([C:11]2[CH:12]=[C:13]([O:21][CH3:22])[C:14]([O:19][CH3:20])=[C:15]([O:17][CH3:18])[CH:16]=2)[OH:10])[CH:47]=[CH:48][C:49]=1[N+:50]([O-:52])=[O:51]

Participants

5

Reactant 4

HCID 758855-Bromo-1,2,3-trimethoxybenzeneHCID 5462224MagnesiumHCID 114920433-Methoxy-4-nitrobenzaldehydeHCID 69203883(4-Methoxy-3-nitro-phenyl)-(3,4,5-trimethoxy-phenyl)-methanol

Product 1

HCID 69203794(3-Methoxy-4-nitro-phenyl)-(3,4,5-trimethoxy-phenyl)-methanolYield 60%

Procedure

(3-Methoxy-4-nitro-phenyl)-(3,4,5-trimethoxy-phenyl)-methanol was prepared analogously to (4-methoxy-3-nitro-phenyl)-(3,4,5-trimethoxy-phenyl)-methanol using 3,4,5-trimethoxy-bromobenzene (3.0 g, 12.1 mmol), magnesium turning (1.0 g, 24.3 mmol) and 3-methoxy-4-nitro-benzaldehyde (1.8 g, 10.1 mmol). The crude product was purified by flash chromatography (silica gel, Hexane:EtOAc 7:3) to afford (3-methoxy-4-nitro-phenyl)-(3,4,5-trimethoxy-phenyl)-methanol (2.1 g, 60%): 1H NMR (CDCl3) δ 7.82 (d, J=8 Hz, 1H), 7.23 (s, 1H), 6.97 (d, J=8 Hz, 1H), 6.54 (s, 2H), 5.76 (s, 1H), 4.76 (s, 1H), 3.96 (s, 3H), 3.85 (s, 9H).

Workup

  1. customThe crude product was purified by flash chromatography (silica gel, Hexane:EtOAc 7:3)

Sources & evidence

ORD record
ord-31c490afbcc7433a8bbd292631320193
Source dataset
uspto-grants-2008_12
Patent number
US07470723B2

Reaction notes

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