2-(2,4-Difluorophenyl)-6-hydroxychroman-4-one → 2-(2,4-Difluorophenyl)chroman-4,6-diol

HRID 31279Notes

Reaction equation

HRID 31279 reaction equation
C1(C2CC(O)C3C(=CC=C(O)C=3)O2)C=CC=CC=1.[F:19][C:20]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=1[CH:27]1[CH2:36][C:35](=[O:37])[C:34]2[C:29](=[CH:30][CH:31]=[C:32]([OH:38])[CH:33]=2)[O:28]1>>[F:19][C:20]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=1[CH:27]1[CH2:36][CH:35]([OH:37])[C:34]2[C:29](=[CH:30][CH:31]=[C:32]([OH:38])[CH:33]=2)[O:28]1

Participants

3

Reactant 2

HCID 179784512-(2,4-Difluorophenyl)-6-hydroxychroman-4-oneHCID 179786312-Phenylchroman-4,6-diol

Product 1

HCID 179785742-(2,4-Difluorophenyl)chroman-4,6-diol

Procedure

2-(2,4-Difluorophenyl)chroman-4,6-diol was prepared as described for 2-phenylchroman-4,6-diol in Example 8(a) starting from 1,47 g of 2-(2,4-difluorophenyl)-6-hydroxychroman-4-one. 1H NMR (400 MHz, d6-DMSO) δ: 8.86 (s, 1H), 7.61 (m, 1H), 7.28 (m, 1H), 7.14 (m, 1H), 6.88 (d, 1H, J 2.7 Hz), 6.59 (d, 1H, J 8.9 Hz), 6.54 (dd, 1H, J 8.9, 2.7 Hz), 5.46 (s, 1H), 5.32 (dd, 1H, J 11.9, 1.4 Hz), 4.88 (m, 1H), 2.24 (m, 1H), 1.99 (m, 1H).

Sources & evidence

ORD record
ord-01c4cc2bd94441f99f2dbaf5af0a5a0d
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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