Water → 5-(Methylsulfonyl)-2-(4-((trifluoromethyl)thio)phenoxy)pyridine

HRID 2290399Notes

Reaction equation

HRID 2290399 reaction equation
[F:1][C:2]([F:12])([F:11])[S:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.CC([O-])(C)C.[K+].CS([C:23]1[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][N:24]=1)(=O)=O.O>C1COCC1>[CH3:32][S:29]([C:26]1[CH:27]=[CH:28][C:23]([O:10][C:7]2[CH:6]=[CH:5][C:4]([S:3][C:2]([F:11])([F:1])[F:12])=[CH:9][CH:8]=2)=[N:24][CH:25]=1)(=[O:31])=[O:30]

Participants

6

Reactant 4

HCID 962WaterHCID 38151584-(Trifluoromethylsulfanyl)phenolHCID 131026752,5-Bis(methylsulfonyl)pyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 131026905-(Methylsulfonyl)-2-(4-((trifluoromethyl)thio)phenoxy)pyridineYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 4.95 g of 4-(trifluoromethylthio)phenol dissolved in a 20 ml THF/20 ml DMSO mixture was added 2.9 g of t-BuOK and then 6.0 g of 2,5-bis(methylsulfonyl)pyridine, and the resulting mixture heated at 58° C. for 11/2 hrs. The reaction mixture was cooled to room temperature and added to approximately 3 to 4 volumes of water. The yellow-brown precipitate that formed was removed by filtration and then recrystallized from CH2Cl2 /ethanol. The purified product, 5-(methylsulfonyl)-2-(4-((trifluoromethyl)thio)phenoxy)pyridine, (60% yield), was recovered as tiny cream-white plates, m.p. 134°-135° C.

Workup

  1. customThe yellow-brown precipitate that formed
  2. customwas removed by filtration
  3. customrecrystallized from CH2Cl2 /ethanol

Sources & evidence

ORD record
ord-cd1f68a202af4a62b731028261db1275
Source dataset
uspto-grants-1986_10
Patent number
US04616087

Reaction notes

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