1-Bromo-3,5-dimethoxybenzene → HCID 69202543, compound

HRID 971040Notes

Reaction equation

HRID 971040 reaction equation
NC1C=C(C(C2C=CC(OC)=C(OC)C=2)=CC#N)C=CC=1OC.[CH3:24][O:25][C:26]1[CH:27]=[C:28](Br)[CH:29]=[C:30]([O:32][CH3:33])[CH:31]=1.[Mg].[CH3:36][O:37][C:38]1[CH:39]=[C:40]([CH:43]=[CH:44][C:45]=1[N+:46]([O-:48])=[O:47])[CH:41]=[O:42]>>[CH3:36][O:37][C:38]1[CH:39]=[C:40]([CH:41]([C:28]2[CH:27]=[C:26]([O:25][CH3:24])[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=2)[OH:42])[CH:43]=[CH:44][C:45]=1[N+:46]([O-:48])=[O:47]

Participants

5

Reactant 4

HCID 6391871-Bromo-3,5-dimethoxybenzeneHCID 5462224MagnesiumHCID 114920433-Methoxy-4-nitrobenzaldehydeHCID 689400613-(3-Amino-4-methoxy-phenyl)-3-(3,4-dimethoxy-phenyl)-acrylonitrile

Product 1

HCID 69202543HCID 69202543, compoundYield 73%

Procedure

(3-Methoxy-4-nitro-phenyl)-(3,5-dimethoxy-phenyl)-methanol was prepared analogously to 3-(3-amino-4-methoxy-phenyl)-3-(3,4-dimethoxy-phenyl)-acrylonitrile using 3,5-dimethoxy-bromobenzene (4.4 g, 20.1 mmol), magnesium turning (1.0 g, 20.1 mmol) and 3-methoxy-4-nitro-benzaldehyde (3.0 g, 16.8 mmol) to afford (3-methoxy-4-nitro-phenyl)-(3,5-dimethoxy-phenyl)-methanol (3.9 g, 73%): 1H NMR (CDCl3) δ 7.79 (d, J=8 Hz, 1H), 7.22 (s, 1H), 7.00-6.99 (dd, J=2, 9.1 Hz, 1H), 6.48 (d, J=2 Hz, 2H), 6.40 (d, J=2 Hz, 1H), 5.75 (d, J=3 Hz, 1H), 3.96 (s, 3H), 3.77 (s, 6H), 2.45 (d, J=2 Hz, 1H).

Sources & evidence

ORD record
ord-b6cf8dea94374faeb38a9093c8780e6d
Source dataset
uspto-grants-2007_12
Patent number
US07312241B2

Reaction notes

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