2-(4-Fluorophenyl)chroman-6-ol → HCID 86608640, compound

HRID 1455048Notes

Reaction equation

HRID 1455048 reaction equation
FC1C=CC(C2CCC3C(=CC=C(O)C=3)O2)=CC=1.[N+:19]([C:22]1[CH:23]=[CH:24][C:25]([O:28][C:29]2[CH:30]=[C:31]3[C:36](=[CH:37][CH:38]=2)[O:35][CH:34]([C:39]2[CH:44]=[CH:43][C:42]([O:45][C:46]4[CH:51]=[CH:50][C:49]([N+:52]([O-:54])=[O:53])=[CH:48][N:47]=4)=[CH:41][CH:40]=2)[CH2:33][CH:32]3O)=[N:26][CH:27]=1)([O-:21])=[O:20]>>[N+:52]([C:49]1[CH:50]=[CH:51][C:46]([O:45][C:42]2[CH:43]=[CH:44][C:39]([CH:34]3[CH2:33][CH2:32][C:31]4[C:36](=[CH:37][CH:38]=[C:29]([O:28][C:25]5[CH:24]=[CH:23][C:22]([N+:19]([O-:21])=[O:20])=[CH:27][N:26]=5)[CH:30]=4)[O:35]3)=[CH:40][CH:41]=2)=[N:47][CH:48]=1)([O-:54])=[O:53]

Participants

3

Reactant 2

HCID 179784812-(4-Fluorophenyl)chroman-6-olHCID 86608641HCID 86608641, compound

Product 1

HCID 86608640HCID 86608640, compound

Procedure

2-{2-[4-(5-Nitropyridin-2-yloxy)-phenyl]-chroman-6-yloxy}-5-nitropyridine was prepared as described for 2-(4-fluorophenyl)chroman-6-ol in Example 2(c) but starting from 6-(5-nitropyridin-2-yloxy)-2-[4-(5-nitropyridin-2-yloxy)phenyl]-chroman-4-ol. 1H NMR (400 MHz, d6-DMSO) δ: 9.05 (d, 2H, J 2.9 Hz), 8.65-8.58 (m, 2H), 7.58-7.55 (m, 2H), 7.30-7.26 (m, 3H), 7.20 (d, 1H, J 9.1 Hz), 7.03-6.91 (m, 3H) 5.20 (dd, 1H, J 2.0, 10.1 Hz), 3.06-2.97 (m, 1H), 2.81-2.75 (m, 1H), 2.26-2.21 (m, 1H), 2.11-2.02 (m, 1H).

Sources & evidence

ORD record
ord-664728e3e47f4cc9aee6cd18af8279dd
Source dataset
uspto-grants-2009_01
Patent number
US07482340B2

Reaction notes

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