Benzonitrile, 4-chloro-3-nitro- → 4-Cyano-2-nitro-1-(2-phenylchroman-6-yloxy)-benzene

HRID 31231

Reaktionsgleichung

Reaktionsgleichung von HRID 31231
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[O:17][CH:16]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:15][CH2:14]2)([O-:3])=[O:2].OC1C=C2C(=CC=1)OC(C1C=CC=CC=1)CC2.[OH-].[K+].ClC1C=CC([C:51]#[N:52])=CC=1[N+]([O-])=O>CS(C)=O>[C:51]([C:8]1[CH:7]=[CH:6][C:5]([O:10][C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[O:17][CH:16]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:15][CH2:14]3)=[C:4]([N+:1]([O-:3])=[O:2])[CH:9]=1)#[N:52]

Komponenten

6

Edukt 4

HCID 13655Benzonitrile, 4-chloro-3-nitro-HCID 14797Potassium HydroxideHCID 179784752-Nitro-1-(2-phenylchroman-6-yloxy)-benzeneHCID 212875382-Phenylchroman-6-ol

Produkt 1

HCID 179785464-Cyano-2-nitro-1-(2-phenylchroman-6-yloxy)-benzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

4-Cyano-2-nitro-1-(2-phenylchroman-6-yloxy)-benzene was prepared as described for 2-nitro-1-(2-phenylchroman-6-yloxy)-benzene in Example 29(a) except that 6-hydroxyflavane (0.453 g) was used in 10 ml of dry DMSO under nitrogen. Also KI (0.498 g) and KOH (0.224 g) and 4-chloro-3-nitro benzonitrile (0.365 mg) were added in similar manner. Product was purified by column chromatography (CH2Cl2:n-heptane/90:10 as the eluant). 1H-NMR (400 MHz; d6-DMSO): δ 8.64 (d, 1H, J=2.0 Hz), 8.06 (dd, 1H, J=8.8 Hz, J=2.1 Hz), 7.08 (d, 1H, J=8.8 Hz), 7.07-6.93 (m, 3H), 5.15 (dd, 1H, J=10.1 Hz, J=2.1 Hz), 3.05-2.91 (m, 1H), 2.82-2.70 (m, 1H), 2.24-2.12 (m, 1H), 2.08-1.92 (m, 1H).

Aufarbeitung

  1. customProduct was purified by column chromatography (CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-68c111e087094d4ab554340363dcb403
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425568B2

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