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

HRID 1758006Notes

Reaction equation

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]

Participants

Conditions

Temperature: 170 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-53c480b956914e26b5bad097cc994a91
Source dataset: uspto-grants-1983_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04371537

Reaction notes

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