Phenol → 2-Chloro-6-phenoxy-4-(4-phenoxyphenyl)nicotinonitrile

HRID 81023Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 81023
[Cl:1][C:2]1[N:9]=[C:8](Cl)[CH:7]=[C:6]([C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:13][CH:12]=2)[C:3]=1[C:4]#[N:5].[C:24]1([OH:30])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O.C(OCC)(=O)C>[Cl:1][C:2]1[N:9]=[C:8]([O:30][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:7]=[C:6]([C:11]2[CH:12]=[CH:13][C:14]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:15][CH:16]=2)[C:3]=1[C:4]#[N:5]

Komponenten

6

Edukt 3

HCID 996PhenolHCID 10796Cesium carbonateHCID 866656822,6-Dichloro-4-(4-phenoxyphenyl)nicotinonitrile

Produkt 1

HCID 866656842-Chloro-6-phenoxy-4-(4-phenoxyphenyl)nicotinonitrileAusbeute 101 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 2,6-dichloro-4-(4-phenoxyphenyl)nicotinonitrile (51 mg, 0.149 mmol, from Step 2 of Example 8), phenol (15.47 mg, 0.164 mmol) and cesium carbonate (97 mg, 0.299 mmol) in DMSO (1.5 mL) was stirred at room temperature for 15 h. The mixture was diluted with ethyl acetate (60 mL), washed with water (2×5 mL), brine (5 mL), dried (MgSO4) and concentrated. Silica gel chromatography, eluting with 0% to 20% ethyl acetate in hexanes, gave 2-chloro-6-phenoxy-4-(4-phenoxyphenyl)nicotinonitrile as a white solid (60 mg, 75% yield). 1H NMR (500 MHz, CDCl3) δ ppm 7.52-7.73 (2H, m), 7.37-7.52 (4H, m), 7.25-7.36 (1H, m), 7.20-7.24 (1H, m), 7.08-7.18 (4H, m), 6.87 (1H, s); MS (ES+) m/z: 399 (M+H); LC retention time: 4.283 min (analytical HPLC Method A).

Aufarbeitung

  1. washwashed with water (2×5 mL), brine (5 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. washSilica gel chromatography, eluting with 0% to 20% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-e14ae2925781465bbf3b100ee2e37a9e
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846673B2

Notizen zur Reaktion

Wird geladen…