Ethylene Glycol → Benzonitrile, 3-(phenylthio)-

HRID 2180667

Reaktionsgleichung

Reaktionsgleichung von HRID 2180667
I[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].[C:10]1([SH:16])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C([O-])([O-])=O.[K+].[K+].C(O)CO>[Cu]I.CC(O)C>[C:10]1([S:16][C:2]2[CH:9]=[CH:8][CH:7]=[C:4]([C:5]#[N:6])[CH:3]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Komponenten

7

Edukt 4

HCID 174Ethylene GlycolHCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 1443413-Iodobenzonitrile

Produkt 1

HCID 11298792Benzonitrile, 3-(phenylthio)-Ausbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

The general procedure in example 39 was followed. 3-Iodobenzonitrile (229 mg, 1.0 mmol), thiophenol (103 μL, 1.0 mmol), CuI (10 mg, 0.05 mmol), K2CO3 (276 mg, 2.0 mmol), ethylene glycol (111 μL, 2.0 mmol) and 2-propanol (1.0 mL) were used to obtain the 3-cyanophenyl phenyl sulfide (181 mg, 86% yield) as colorless liquid. Column chromatography solvent (hexane/ethyl acetate=25/1). Rf=0.4 (hexane/ethyl acetate=20/1). 1H NMR (CDCl3, 300 MHz) δ 7.30-7.45 (m, 9 H). 13C NMR (CDCl3, 75 MHz) δ 140.2, 133.6, 132.9, 132.3, 131.7, 130.0, 129.7, 129.6, 129.1, 118.5, 113.5. MS (EI) m/z (relative intensity) 211 (30), 185 (20), 134 (100).

Quellen und Nachweise

ORD-Eintrag
ord-5ed6aace39d7470b84cd3106e635bfdf
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06888032B2

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