Potassium Carbonate → Benzonitrile, 4-(4-(methylsulfonyl)phenoxy)-

HRID 1702816

Reaktionsgleichung

Reaktionsgleichung von HRID 1702816
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8](F)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[C:12]([C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)#[N:13].C([O-])([O-])=O.[K+].[K+].S1(CCCC1)(=O)=O.[OH-].[Na+]>O>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([O:20][C:17]2[CH:18]=[CH:19][C:14]([C:12]#[N:13])=[CH:15][CH:16]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Komponenten

7

Edukt 5

HCID 11430Potassium CarbonateHCID 130194-CyanophenolHCID 14798Sodium HydroxideHCID 31347SulfolaneHCID 679941-Fluoro-4-(methylsulphonyl)benzene

Produkt 1

HCID 514876Benzonitrile, 4-(4-(methylsulfonyl)phenoxy)-Ausbeute 28,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A mixture of 5.23 g (0.0300 mole) of 4-fluorophenyl methyl sulfone, 7.15 g (0.0600 mole) of 4-cyanophenol, 8.29 g (0.0600 mole) of anhydrous K2CO3 and 90 ml of sulfolane was heated at 150° C. for 3.5 hrs. The mixture was cooled and poured into a solution of 100 ml of 20% aqueous NaOH and 500 ml of water. Extraction of the basic solution with diethyl ether afforded 2.3 g (28% yield) of product after removal of solvent in vacuo. The product was purified by column chromatography using silica gel as the support and chloroform as the eluent. The purified 4-(4-(methylsulfonyl)phenoxy)benzonitrile was found to have a melting point of 127°-128.5° C.

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. extractionExtraction of the basic solution with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-efe46c6ca7d54b3abdabee5361053836
Quelldatensatz
uspto-grants-1982_09
Patentnummer
US04349568

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