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

HRID 76823

Reaction equation

HRID 76823 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]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[C:18]([O:26][CH3:27])[CH:17]=1)=[O:15]>>[CH3:1][O:2][C:3]1[C:4]2[CH:13]=[C:14]([C:16]3[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[C:18]([O:26][CH3:27])[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 36857322-Bromo-1-(3,4,5-trimethoxyphenyl)ethanone

Product 1

HCID 545908704,6-Dimethoxy-2-(3,4,5-trimethoxyphenyl)-1-benzofuranYield 75%

Procedure

This compound was prepared using Method A from 3,5-dimethoxyphenol and 2-bromo-1-(3,4,5-trimethoxyphenyl)ethanone: Yield 75% following procedure A.2; m.p. 131-132° C.; IR 2960, 1619, 1497, 1227, 1203, 1134, 1110 cm−1; 1H-NMR (500 MHz, δ ppm, CDCl3) 7.04 (s, 2H), 7.00 (s, 1H), 6.74 (s, 1H), 6.36 (d, J=1.8 Hz, 1H), 3.97 (s, 6H), 3.95 (s, 3H), 3.91 (s, 3H), 3.89 (s, 3H); 13C-NMR (126 MHz, δ ppm, CDCl3) 159.4, 156.7, 153.8, 153.7, 153.6, 138.4, 126.6, 113.5, 101.9, 98.7, 94.6, 88.5, 61.2, 56.4, 56.0, 55.8.

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-8b865e356b1a46beaac9524639b9f9ac
Source dataset
uspto-grants-2014_09
Patent number
US08835659B2

Linked notes

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