2-Acetylhydroquinone → 2-(2,3-Difluorophenyl)-6-hydroxychroman-4-one

Reaktionsgleichung

[F:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:17][C:16](=[O:18])[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([OH:19])[CH:14]=3)[O:9]2)[CH:5]=[CH:6][CH:7]=1.OC1C=CC(O)=CC=1C(=O)C.[F:31]C1C(F)=CC=CC=1C=O>>[F:31][C:3]1[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=1[CH:8]1[CH2:17][C:16](=[O:18])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([OH:19])[CH:14]=2)[O:9]1

Komponenten

Edukt 3

HCID 102792-Acetylhydroquinone

HCID 1376642,3-Difluorobenzaldehyde

HCID 179784652-(3-Fluorophenyl)-6-hydroxychroman-4-one

Produkt 1

HCID 179785142-(2,3-Difluorophenyl)-6-hydroxychroman-4-one

Versuchsvorschrift

2-(2,3-Difluorophenyl)-6-hydroxychroman-4-one was prepared as described for 2-(3-fluorophenyl)-6-hydroxychroman-4-one in Example 9(a) starting from 3.0 g of 2′,5′-dihydroxyacetophenone and 2.6 ml of 2,3-difluorobenzaldehyde. 1H NMR (400 MHz, d6-DMSO) δ: 9.51 (s, 1H), 7.53-7.46 (m, 2H), 7.31 (m, 1H), 7.14 (d, 1H, J 3.0 Hz), 7.05 (dd, 1H, 3 8.8, 3.0 Hz), 6.96 (d, 1H, J 8.8 Hz), 5.82 (dd, 1H, J 13.4, 2.8 Hz), 3.26 (dd, 1H, J −16.9, 13.4 Hz), 2.79 (dd, 1H, J −16.9, 2.8 Hz).