4-Chloro-alpha,alpha,alpha-trifluoro-3-nitrotoluene → 2-Nitro-1-(2-phenylchroman-6-yloxy)-4-trifluoromethylbenzene

HRID 31227

Reaktionsgleichung

Reaktionsgleichung von HRID 31227
[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:53]([F:56])([F:55])[F:54])=CC=1[N+]([O-])=O>CS(C)=O>[N+:1]([C:4]1[CH:9]=[C:8]([C:53]([F:56])([F:55])[F:54])[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]

Komponenten

6

Edukt 4

HCID 84624-Chloro-alpha,alpha,alpha-trifluoro-3-nitrotolueneHCID 14797Potassium HydroxideHCID 179784752-Nitro-1-(2-phenylchroman-6-yloxy)-benzeneHCID 212875382-Phenylchroman-6-ol

Produkt 1

HCID 179786542-Nitro-1-(2-phenylchroman-6-yloxy)-4-trifluoromethylbenzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

2-Nitro-1-(2-phenylchroman-6-yloxy)-4-trifluoromethylbenzene was prepared as described for 2-nitro-1-(2-phenylchroman-6-yloxy)-benzene in Example 29(a) except that 6-hydroxyflavane (0.339 g) was used in 7 ml of dry DMSO under nitrogen. Also KI (0.374 g) and KOH (0.168 g) and 4-chloro-3-nitro-1-trifluoromethylbenzene (0.24 ml) were added in similar manner. Product was purified by column chromatography (CH2Cl2:n-heptane/60:40). 1H-NMR (300 MHz; d6-DMSO): δ 8.44 (d, 1H, J=2.1 Hz), 7.99 (dd, 1H, J=9.0 Hz; J=2.2 Hz), 7.51-7.29 (m, 5H), 7.15 (d, 1H, J=8.7 Hz), 7.09-6.91 (m, 3H), 5.15 (dd, 1H, J=10.1 Hz; J=2.3 Hz), 3.08-2.90 (m, 1H), 2.83-2.68 (m, 1H), 2.25-2.11 (m, 1H), 2.09-1.91 (m, 1H).

Aufarbeitung

  1. customProduct was purified by column chromatography (CH2Cl2:n-heptane/60:40)

Quellen und Nachweise

ORD-Eintrag
ord-dfbe175640974ad8a50519caad81cf98
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07425568B2

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