Bromomethyl 4-methoxyphenyl ketone → 2-(4-Hydroxyphenyl)-1-benzofuran-4,6-diol

HRID 76828Notes

Reaction equation

HRID 76828 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]=[CH:20][C:19]([O:22]C)=[CH:18][CH:17]=1)=[O:15]>>[OH:22][C:19]1[CH:18]=[CH:17][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:21][CH:20]=1

Participants

3

Reactant 2

HCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 103833,5-Dimethoxyphenol

Product 1

HCID 545909582-(4-Hydroxyphenyl)-1-benzofuran-4,6-diolYield 93%

Procedure

This compound was prepared using Method A from 3,5-dimethoxyphenol and 2-bromo-1-(4-methoxyphenyl)ethanone: Yield 93% following procedures A.2 and A.5; m.p. 216-217° C.; IR 3309, 1613, 1510, 1439, 1241, 1134, 1064 cm−1; 1H-NMR (500 MHz, δ ppm, DMSO-d6) 9.76 (5, 1H), 9.67 (s, 1H), 9.28 (s, 1H), 7.59 (d, J=8.7 Hz, 2H), 6.97 (s, 1H), 6.83 (d, J=8.7 Hz, 2H), 6.39 (d, J=0.8 Hz, 1H), 6.16 (d, J=1.8 Hz, 1H); 13C-NMR (126 MHz, δ ppm, CD3OD) 158.7, 158.4, 157.3, 154.8, 152.1, 126.8, 124.3, 116.7, 113.1, 98.8, 97.4, 90.9.

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-cb7b16b6b8fc4223b3d559e26a180a60
Source dataset
uspto-grants-2014_09
Patent number
US08835659B2

Reaction notes

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