2-(3-Bromophenyl)chroman-4,6-diol → 2-(3-Bromophenyl)-6-(5-nitropyridin-2-yloxy)chroman-4ol

HRID 31262Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[CH:6][C:7](OC2C=C3C(=CC=2)OC(C2C=CC=CC=2)CC3)=[N:8][CH:9]=1)([O-:3])=[O:2].[Br:27][C:28]1[CH:29]=[C:30]([CH:34]2[CH2:43][CH:42]([OH:44])[C:41]3[C:36](=[CH:37][CH:38]=[C:39]([OH:45])[CH:40]=3)[O:35]2)[CH:31]=[CH:32][CH:33]=1>>[Br:27][C:28]1[CH:29]=[C:30]([CH:34]2[CH2:43][CH:42]([OH:44])[C:41]3[C:36](=[CH:37][CH:38]=[C:39]([O:45][C:7]4[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]=4)[CH:40]=3)[O:35]2)[CH:31]=[CH:32][CH:33]=1

Participants

Reactant 2

HCID 179784762-(3-Bromophenyl)chroman-4,6-diol

HCID 17978512Orm-10103

Product 1

HCID 179786512-(3-Bromophenyl)-6-(5-nitropyridin-2-yloxy)chroman-4ol

Procedure

2-(3-Bromophenyl)-6-(5-nitropyridin-2-yloxy)chroman-4ol was prepared as described for 5-nitro-2-(2-phenylchroman-6-yloxy)pyridine in Example 1(b) starting from 215 mg of 2-(3-bromophenyl)chroman-4,6-diol (Example 15(b)). The product was recrystallised from a mixture of 2-propanol and acetone. 1H NMR (300 MHz, d6-DMSO) δ: 9.04 (d, 1H, J 2.8 Hz), 8.61 (dd, 1H, J 9.1, 2.8 Hz), 7.69 (m, 1H), 7.58-7.50 (m, 2H), 7.40 (m, 1H), 7.25 (d, 1H, J 2.7 Hz), 7.22 (d, 1H, 9.1 Hz), 7.02 (dd, 1H, J 8.8, 2.7 Hz), 6.91 (d, 1H, J 8.8 Hz), 5.65 (d, 1H, J 6.4 Hz), 5.33 (d, 1H, J 10.8 Hz), 4.97 (m, 1H), 2.36 (m, 1H), 1.94 (m, 1H).

Workup

customThe product was recrystallised from a mixture of 2-propanol and acetone

Sources & evidence

ORD record: ord-ef5486330177498ab96eefaa21afc1e3
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07425568B2

Reaction notes

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