Bromomethyl 4-methoxyphenyl ketone → 3-(4-Hydroxyphenyl)-1-benzofuran-4,6-diol

HRID 76834Notes

Reaction equation

HRID 76834 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([OH:11])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.BrC[C:14]([C:16]1[CH:21]=[CH:20][C:19]([O:22]C)=[CH:18][CH:17]=1)=O>>[OH:22][C:19]1[CH:20]=[CH:21][C:16]([C:14]2[C:6]3=[C:5]([OH:11])[CH:4]=[C:3]([OH:2])[CH:8]=[C:7]3[O:9][CH:10]=2)=[CH:17][CH:18]=1

Participants

3

Reactant 2

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

Product 1

HCID 545909633-(4-Hydroxyphenyl)-1-benzofuran-4,6-diolYield 38%

Procedure

This compound was prepared using Method B from 3,5-dimethoxyphenol and 2-bromo-1-(4-methoxyphenyl)ethanone: Yield 38% following procedures B.2, B.3 and B.5; m.p. 220° C. (dec.); IR 3460, 3373, 2914, 1635, 1518, 1229, 1133, 1055 cm−1; 1H-NMR (500 MHz, δ ppm, DMSO-d6) 9.75 (s, 1H), 9.36 (s, 1H), 9.33 (s, 1H), 7.62 (s, 1H), 7.46 (d, J=8.5 Hz, 2H), 6.75 (d, J=8.5 Hz, 2H), 6.37 (d, J=1.7 Hz, 1H), 6.21 (d, J=1.6 Hz, 1H); 13C-NMR (126 MHz, δ ppm, CD3OD) 160.2, 157.7, 157.5, 153.6, 139.7, 131.4, 125.4, 124.1, 115.9, 109.6, 99.0, 90.9.

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-bddb8cc8bdd043e7aabe17da1254fadb
Source dataset
uspto-grants-2014_09
Patent number
US08835659B2

Reaction notes

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