2,4,5-Trichlorophenol → 5-(Ethylsulfonyl)-2-(2,4,5-trichlorophenoxy)pyridine

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Reaktionsgleichung

C(S([C:6]1[CH:11]=[CH:10][C:9]([S:12]([CH2:15][CH3:16])(=[O:14])=[O:13])=[CH:8][N:7]=1)(=O)=O)C.[Cl:17][C:18]1[CH:23]=[C:22]([Cl:24])[C:21]([Cl:25])=[CH:20][C:19]=1[OH:26].C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+]>S1(CCCC1)(=O)=O>[CH2:15]([S:12]([C:9]1[CH:10]=[CH:11][C:6]([O:26][C:19]2[CH:20]=[C:21]([Cl:25])[C:22]([Cl:24])=[CH:23][C:18]=2[Cl:17])=[N:7][CH:8]=1)(=[O:13])=[O:14])[CH3:16]

Komponenten

Reaktionsbedingungen

Temperatur: 170 °C

Versuchsvorschrift

In 70 ml of sulfolane were mixed 10.5 g of 2,5-bis(ethylsulfonyl)pyridine, 15.8 g of 2,4,5-trichlorophenol and 11.06 g of potassium carbonate. The mixture was warmed gradually to 170° C. and maintained at that temperature for 2 hrs. The reaction mixture was cooled and then poured into 300 g of ice containing 4 g of sodium hydroxide. The aqueous solution was extracted with ether. The organic layer was washed with water, dried over MgSO4 and concentrated. The product was purified using a Water's Prep LC 500 instrument with 10% ethyl acetate/90% hexane as eluent. Recrystallization from diethyl ether gave 2.8 g, (19% yield), of purified 5-(ethylsulfonyl)-2-(2,4,5-trichlorophenoxy)pyridine, m.p. 120°-122° C.

Aufarbeitung

temperaturemaintained at that temperature for 2 hrs
temperatureThe reaction mixture was cooled
extractionThe aqueous solution was extracted with ether
washThe organic layer was washed with water
dry with materialdried over MgSO4
concentrationconcentrated
customThe product was purified
customRecrystallization from diethyl ether

Quellen und Nachweise

ORD-Eintrag: ord-53c480b956914e26b5bad097cc994a91
Quelldatensatz: uspto-grants-1983_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04371537

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