2-(2,5-Difluorophenyl)-6-hydroxychroman-4-one → 2-(2,5-Difluorophenyl)chroman-4,6-diol

HRID 31192Notes

Reaction equation

HRID 31192 reaction equation
C1(C2CC(O)C3C(=CC=C(O)C=3)O2)C=CC=CC=1.[F:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[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]=[CH:24][C:23]([F:26])=[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 179785912-(2,5-Difluorophenyl)-6-hydroxychroman-4-oneHCID 179786312-Phenylchroman-4,6-diol

Product 1

HCID 179785942-(2,5-Difluorophenyl)chroman-4,6-diol

Procedure

2-(2,5-Difluorophenyl)chroman-4,6-diol was prepared as described for 2-phenylchroman-4,6-diol in Example 8(a) starting from 1.0 g of 2-(2,5-difluorophenyl)-6-hydroxychroman-4-one. 1H NMR (400 MHz, d6-DMSO) δ: 8.87 (s, 1H), 7.39-7.22 (m, 3H), 6.89 (d, 1H, J 2.8 Hz), 6.63 (d, 1H, J 8.7 Hz), 6.56 (dd, 1H, J 8.7, 2.8 Hz), 5.50 (d, 1H, J 6.8 Hz), 5.35 (d, 1H, J 11.2 Hz), 4.89 (m, 1H), 2.28 (m, 1H), 1.95 (m, 1H).

Sources & evidence

ORD record
ord-2ec59b0dab0447d49ceea4b84320a6cf
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

Loading…