2-(3-Fluorophenyl)chroman-6-ol → 2-(3,5-Difluorophenyl)chroman-6-ol

HRID 31189Notes

Reaction equation

HRID 31189 reaction equation
FC1C=C(C2CCC3C(=CC=C(O)C=3)O2)C=CC=1.[F:19][C:20]1[CH:21]=[C:22]([CH:27]2[CH2:36][CH:35](O)[C:34]3[C:29](=[CH:30][CH:31]=[C:32]([OH:38])[CH:33]=3)[O:28]2)[CH:23]=[C:24]([F:26])[CH:25]=1>>[F:19][C:20]1[CH:21]=[C:22]([CH:27]2[CH2:36][CH2:35][C:34]3[C:29](=[CH:30][CH:31]=[C:32]([OH:38])[CH:33]=3)[O:28]2)[CH:23]=[C:24]([F:26])[CH:25]=1

Participants

3

Reactant 2

HCID 179784712-(3-Fluorophenyl)chroman-6-olHCID 179785182-(3,5-Difluorophenyl)chroman-4,6-diol

Product 1

HCID 179785282-(3,5-Difluorophenyl)chroman-6-ol

Procedure

2-(3,5-Difluorophenyl)chroman-6-ol was prepared as described for 2-(3-fluorophenyl)chroman-6-ol in Example 9(c) starting from 500 mg of 2-(3,5-difluorophenyl)chroman-4,6-diol. 1H NMR (300 MHz, d6-DMSO) δ: 8.82 (s, 1H), 7.20-7.14 (m, 3H), 6.68 (d, 1H, J 8.6 Hz), 6.53 (d, 1H, J 2.9 Hz), 6.50 (dd, 1H, J 8.6, 2.9 Hz), 5.05 (dd, 1H, J 9.8, 2.2 Hz), 2.88 (ddd, 1H, J −16.7, 10.8, 5.9 Hz), 2.62 (ddd, 1H, J −16.7, 8.9, 5.0 Hz), 2.15 (m, 1H), 1.93 (m, 1H).

Sources & evidence

ORD record
ord-29dc0df7004742dbb6e77127955bf6b8
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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