Cesium carbonate → 4-(2-Methoxycarbonylphenyl)thio-2,3,5,6-tetrafluoropyridine

HRID 1636303Notes

Reaction equation

HRID 1636303 reaction equation
[C:1]([O:10][CH3:11])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[SH:4].[F:12][C:13]1[N:18]=[C:17]([F:19])[C:16]([F:20])=[C:15](F)[C:14]=1[F:22].C(=O)([O-])[O-].[Cs+].[Cs+].[OH-].[K+]>CN(C=O)C.C(OCC)(=O)C>[CH3:11][O:10][C:1]([C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[S:4][C:15]1[C:14]([F:22])=[C:13]([F:12])[N:18]=[C:17]([F:19])[C:16]=1[F:20])=[O:9]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 14797Potassium HydroxideHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 69690Pentafluoropyridine

Product 1

HCID 154534494-(2-Methoxycarbonylphenyl)thio-2,3,5,6-tetrafluoropyridineYield 98%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl thiosalicylate (1.0 g, 5.9 mmol) in dry DMF (15 mL) at 0° C. was added pentafluoropyridine (1.2 g, 7.1 mmol) and cesium carbonate (2.5 g, 7.7 mmol). The resultant mixture was stirred at ambient temperature for 5 hours then poured into 100 mL of 0.5 M aqueous KOH solution and 100 mL of ethyl acetate. The aqueous layer was separated and extracted with another 100 mL of ethyl acetate. The combined organic extracts were washed with 0.5 M aqueous KOH solution (100 mL) then brine (100 mL), dried over MgSO4, filtered, and concentrated in vacuo to afford 1.8 g (98% yield) of 4-(2-methoxycarbonylphenyl)thio-2,3,5,6-tetrafluoropyridine as a crystalline solid, NMR (CDCl3) 8.1 (dd, 1), 7.4 (m, 1), 7.4 (tt, 1), 7.0 (d, 1), 4.0 (s, 3) ppm.

Workup

  1. customThe aqueous layer was separated
  2. extractionextracted with another 100 mL of ethyl acetate
  3. washThe combined organic extracts were washed with 0.5 M aqueous KOH solution (100 mL)
  4. dry with materialbrine (100 mL), dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a574070465e946288d30491e564be693
Source dataset
uspto-grants-2000_03
Patent number
US06034084

Reaction notes

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