2-(3-Fluorophenyl)chroman-6-ol → 2-(2,4-Dichlorophenyl)chroman-6-ol

HRID 31181Notes

Reaction equation

HRID 31181 reaction equation
FC1C=C(C2CCC3C(=CC=C(O)C=3)O2)C=CC=1.[Cl:19][C:20]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:21]=1[CH:27]1[CH2:36][CH:35](O)[C:34]2[C:29](=[CH:30][CH:31]=[C:32]([OH:38])[CH:33]=2)[O:28]1>>[Cl:19][C:20]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:21]=1[CH:27]1[CH2:36][CH2:35][C:34]2[C:29](=[CH:30][CH:31]=[C:32]([OH:38])[CH:33]=2)[O:28]1

Participants

3

Reactant 2

HCID 179784712-(3-Fluorophenyl)chroman-6-olHCID 179785882-(2,4-Dichlorophenyl)chroman-4,6-diol

Product 1

HCID 179785552-(2,4-Dichlorophenyl)chroman-6-ol

Procedure

2-(2,4-Dichlorophenyl)chroman-6-ol was prepared as described for 2-(3-fluorophenyl)chroman-6-ol in Example 9(c) starting from 625 mg of 2-(2,4-dichlorophenyl)chroman-4,6-diol. 1H NMR (400 MHz, d6-DMSO) δ: 8.85 (s, 1H), 7.65 (d, 1H, J 2.2 Hz), 7.57 (d, 1H, J 8.4 Hz), 7.49 (dd, 1H, J 8.4, 2.2 Hz), 6.67-6.51 (m, 3H), 5.21 (dd, 1H, J 10.3, 2.1 Hz), 2.91 (m, 1H), 2.69 (m, 1H), 2.16 (m, 1H), 1.85 (m, 1H).

Sources & evidence

ORD record
ord-82ce174ba70e4be98d1c09ca94c8842b
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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