3,5-Dimethoxyphenol → 2-(3,5-Dihydroxyphenyl)-1-benzofuran-4,6-diol

HRID 76827Notes

Reaction equation

HRID 76827 reaction equation
C[O:2][C:3]1[CH:4]=[C:5](O)[CH:6]=[C:7]([O:9]C)[CH:8]=1.Br[CH2:13][C:14]([C:16]1[CH:21]=[C:20]([O:22]C)[CH:19]=[C:18]([O:24]C)[CH:17]=1)=[O:15]>>[OH:22][C:20]1[CH:21]=[C:16]([C:14]2[O:15][C:5]3[C:6](=[C:7]([OH:9])[CH:8]=[C:3]([OH:2])[CH:4]=3)[CH:13]=2)[CH:17]=[C:18]([OH:24])[CH:19]=1

Participants

3

Reactant 2

HCID 103833,5-DimethoxyphenolHCID 27569322-Bromo-1-(3,5-dimethoxyphenyl)ethanone

Product 1

HCID 545909572-(3,5-Dihydroxyphenyl)-1-benzofuran-4,6-diolYield 74%

Procedure

This compound was prepared using Method A from 3,5-dimethoxyphenol and 2-bromo-1-(3,5-dimethoxyphenyl)ethanone: Yield 74% following procedures A.2 and A.5; m.p. 244° C. (dec.); IR 3349, 2920, 1610, 1442, 1252, 1134 cm−1; 1H-NMR (500 MHz, δ ppm, DMSO-d6) 9.78 (s, 1H), 9.33 (s, 2H), 9.32 (s, 1H), 7.01 (s, 1H), 6.62 (d, J=2.0, 2H), 6.39 (s, 1H), 6.19-6.15 (m, 2H); 13C-NMR (126 MHz, δ ppm, CD3OD) 160.0, 158.6, 157.9, 154.5, 152.4, 134.1, 112.9, 103.9, 103.4, 99.8, 98.8, 90.8.

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-cf5fe120168047179fb81b5c8a174127
Source dataset
uspto-grants-2014_09
Patent number
US08835659B2

Reaction notes

Loading…