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

HRID 31278

Reaktionsgleichung

Reaktionsgleichung von HRID 31278
FC1C=C(C2CC(=O)C3C(=CC=C(O)C=3)O2)C=CC=1.[OH:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][C:22]=1[C:28](=[O:30])[CH3:29].[F:31][C:32]1[CH:39]=[C:38]([F:40])[CH:37]=[CH:36][C:33]=1[CH:34]=O>>[F:31][C:32]1[CH:39]=[C:38]([F:40])[CH:37]=[CH:36][C:33]=1[CH:34]1[CH2:29][C:28](=[O:30])[C:22]2[C:21](=[CH:26][CH:25]=[C:24]([OH:27])[CH:23]=2)[O:20]1

Komponenten

4

Edukt 3

HCID 102792-AcetylhydroquinoneHCID 737702,4-DifluorobenzaldehydeHCID 179784652-(3-Fluorophenyl)-6-hydroxychroman-4-one

Produkt 1

HCID 179784512-(2,4-Difluorophenyl)-6-hydroxychroman-4-one

Versuchsvorschrift

2-(2,4-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 1,6 ml of 2,4-difluorobenzaldehyde. 1H NMR (400 MHz, d6-DMSO) δ: 9.46 (s, 1H), 7.73 (m, 1H), 7.34 (m, 1H), 7.19 (m, 1H), 7.13 (d, 1H, J 2.9 Hz), 7.04 (dd, 1H, J 8.8, 2.9 Hz), 6.95 (d, 1H, J 8.8 Hz), 5.74 (dd, 1H, J 13.5, 2.8 Hz), 3.28 (dd, 1H, J −16.9, 13.5 Hz), 2.74 (dd, 1H, J −16.9, 2.8 Hz).

Quellen und Nachweise

ORD-Eintrag
ord-356ac7eca04a4a3599f40673b30c5149
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425568B2

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