1-Bromo-3,5-dimethoxybenzene → (3,5-Dimethoxy-phenyl)-(4-methoxy-3-nitro-phenyl)-methanol

HRID 970997Notes

Reaction equation

HRID 970997 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([O:19]C)C(OC)=CC=C(CO)C2)=[CH:5][C:4]=1[N+:21]([O-:23])=[O:22].[CH3:24][O:25][C:26]1[CH:27]=[C:28](Br)[CH:29]=[C:30]([O:32][CH3:33])[CH:31]=1.[Mg].COC1C=CC(C=O)=CC=1[N+]([O-])=O>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:28]2[CH:27]=[C:26]([O:25][CH3:24])[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=2)[OH:19])=[CH:5][C:4]=1[N+:21]([O-:23])=[O:22]

Participants

5

Reactant 4

HCID 6391871-Bromo-3,5-dimethoxybenzeneHCID 7006084-Methoxy-3-nitrobenzaldehydeHCID 5462224MagnesiumHCID 692056553-(4-Methoxy-3-nitro-phenyl)-(3,4-dimethoxy-phenyl)-methanol

Product 1

HCID 69202587(3,5-Dimethoxy-phenyl)-(4-methoxy-3-nitro-phenyl)-methanolYield 60%

Procedure

(4-Methoxy-3-nitro-phenyl)-(3,5-dimethoxy-phenyl)-methanol was prepared analogously to 3-(4-methoxy-3-nitro-phenyl)-(3,4-dimethoxy-phenyl)-methanol using 3,5-dimethoxy-bromobenzene (5.0 g, 23.0 mmol), magnesium turning (0.6 g, 23.0 mmol) and 4-methoxy-3-nitro-benzaldehyde (3.5 g, 19.2 mmol). The crude product was purified by flash chromatography (silica gel, Hexane:EtOAc 1:1) to afford (4-methoxy-3-nitro-phenyl)-(3,5-dimethoxy-phenyl)-methanol (3.7 g, 60%) as an oil: 1H NMR (CDCl3) δ 7.88 (s, 1H), 7.54-7.50 (dd, J=2, 8 Hz, 1H), 7.04 (d, J=8 Hz, 1H), 6.38 (d, J=1 Hz, 1H), 5.72 (d, J=3 Hz, 1H), 3.93 (s, 3H), 3.76 (s, 6H), 2.45 (d, 2 Hz, 1H).

Workup

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

Sources & evidence

ORD record
ord-d8ab7f30f44a410c8c29031d3e1925b7
Source dataset
uspto-grants-2007_12
Patent number
US07312241B2

Reaction notes

Loading…