Acetone → 6-[2-Fluoro-4-(methylsulfonyl)phenyl]-3-pyridinol

HRID 423711Notes

Reaction equation

HRID 423711 reaction equation
O[O:2][S:3]([O-:5])=O.[K+].Cl.[F:8][C:9]1[CH:14]=[C:13](SC)[CH:12]=[CH:11][C:10]=1[C:17]1[N:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1.[CH3:24]C(C)=O>O>[F:8][C:9]1[CH:14]=[C:13]([S:3]([CH3:24])(=[O:5])=[O:2])[CH:12]=[CH:11][C:10]=1[C:17]1[N:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 23707502Potassium hydroxy sulfiteHCID 66672693HCID 66672693, compound

Product 1

HCID 666730256-[2-Fluoro-4-(methylsulfonyl)phenyl]-3-pyridinolYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Oxone® (9.05 g, 14.7 mmol) was added to a solution of 6-[2-fluoro-4-(methylthio)phenyl]-3-pyridinol hydrochloride (prepared as in Example 176, Step 1, 2 g, 7.4 mmol) in acetone (45 mL) and water (15 mL) at room temperature. The mixture was stirred at room temperature overnight. The reaction was filtered to remove the solid, and washed by CH2Cl2. The filtrate was brought to pH=7 with 2M Na2CO3 and was extracted with CH2Cl2. The organic extract was washed with brine, dried over Na2SO4, and evaporated to dryness. The residue was treated with a small amount of CH2Cl2 and sonicated, and then the solid was collected by filtration and washed with a small amount of CH2Cl2. The filtrate was evaporated to dryness again, treated with a small amount of CH2Cl2 and sonicated. The resulting solid was collected and washed by a small amount of CH2Cl2. The solids were combined to give 1.35 g (65%) of 6-[2-fluoro-4-(methylsulfonyl)phenyl]-3-pyridinol as a pink solid.

Workup

  1. filtrationThe reaction was filtered
  2. customto remove the solid
  3. washwashed by CH2Cl2
  4. extractionwas extracted with CH2Cl2
  5. extractionThe organic extract
  6. washwas washed with brine
  7. dry with materialdried over Na2SO4
  8. customevaporated to dryness
  9. additionThe residue was treated with a small amount of CH2Cl2
  10. customsonicated
  11. filtrationthe solid was collected by filtration
  12. washwashed with a small amount of CH2Cl2
  13. customThe filtrate was evaporated to dryness again
  14. additiontreated with a small amount of CH2Cl2
  15. customsonicated
  16. customThe resulting solid was collected
  17. washwashed by a small amount of CH2Cl2

Sources & evidence

ORD record
ord-d7643861644f470fa594411c7b5b1e9f
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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