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

HRID 76835

Reaction equation

HRID 76835 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]=[C:20]([F:22])[CH:19]=[C:18]([F:23])[CH:17]=1)=O>>[F:22][C:20]1[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]=[C:18]([F:23])[CH:19]=1

Participants

3

Reactant 2

HCID 103833,5-DimethoxyphenolHCID 27783312-Bromo-1-(3,5-difluorophenyl)ethanone

Product 1

HCID 545910443-(3,5-Difluorophenyl)-1-benzofuran-4,6-diolYield 50%

Procedure

This compound was prepared using Method B from 3,5-dimethoxyphenol and 2-bromo-1-(3,5-difluorophenyl)ethanone: Yield 50% following procedures B.2, B.3 and B.5; m.p. 149-151° C.; IR 3373, 1629, 1507, 1359, 1255, 1157, 1123, 1031 cm−1; 1H-NMR (500 MHz, δ ppm, DMSO-d6) 10.08 (s, 1H), 9.45 (s, 1H), 8.02 (s, 1H), 7.49 (d, J=7.7 Hz, 2H), 7.13 (t, J=9.4 Hz, 1H), 6.43 (s, 1H), 6.28 (s, 1H); 13C-NMR (75 MHz, δ ppm, CD3OD) 164.3 (dd, J=244.8 Hz, 13.4 Hz), 160.4, 158.1, 153.5, 141.7, 137.8 (t, J=10.7 Hz), 122.6, 112.8 (dd, J=8.1 Hz, 17.6 Hz), 108.4, 102.6 (t, J=25.9 Hz), 99.4, 91.0.

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-7e9d15f317f14675b686424791b40cda
Source dataset
uspto-grants-2014_09
Patent number
US08835659B2

Linked notes

Loading…