3,5-Dimethoxyphenol → 4,6-Dimethoxy-2-(4-nitrophenyl)-1-benzofuran

HRID 76825

Reaction equation

HRID 76825 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](O)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.Br[CH2:13][C:14]([C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1)=[O:15]>>[CH3:1][O:2][C:3]1[C:4]2[CH:13]=[C:14]([C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=3)[O:15][C:5]=2[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1

Participants

3

Reactant 2

HCID 103833,5-DimethoxyphenolHCID 668402-Bromo-4'-nitroacetophenone

Product 1

HCID 545908724,6-Dimethoxy-2-(4-nitrophenyl)-1-benzofuranYield 44%

Procedure

This compound was prepared using Method A from 3,5-dimethoxyphenol and 2-bromo-1-(4-nitrophenyl)ethanone: Yield 44% following procedure A.2; m.p. 192-193° C.; IR 2943, 2914, 1594, 1504, 1319, 1145, 1104 cm−1; 1H-NMR (500 MHz, δ ppm, CDCl3) 8.26 (d, J=8.8 Hz, 2H), 7.88 (d, J=8.8 Hz, 2H), 7.24 (s, 1H), 6.69 (s, 1H), 6.34 (s, 1H), 3.93 (s, 3H), 3.88 (s, 3H); 13C-NMR (75 MHz, δ ppm, DMSO-d6) 160.3, 156.7, 153.6, 150.6, 146.1, 135.9, 124.5, 124.3, 112.4, 103.9, 94.9, 88.5, 55.8, 55.7.

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-63d27701c6d94bc3a73c56a53d3d8157
Source dataset
uspto-grants-2014_09
Patent number
US08835659B2

Linked notes

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