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

HRID 971001Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5](Br)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[Mg].[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][C:24]=1[N+:25]([O-:27])=[O:26])[CH:20]=[O:21]>>[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH:20]([C:5]2[CH:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=2)[OH:21])[CH:22]=[CH:23][C:24]=1[N+:25]([O-:27])=[O:26]

Participants

Reactant 3

HCID 758855-Bromo-1,2,3-trimethoxybenzene

HCID 5462224Magnesium

HCID 114920433-Methoxy-4-nitrobenzaldehyde

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-trimthoxy-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

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

Sources & evidence

ORD record: ord-b3e795fa5a9f4e3cae23162e9bde0248
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07312241B2

Reaction notes

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