Chlorodifluoromethane → HCID 68857309, compound

HRID 491276Notes

Reaction equation

HRID 491276 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[CH:5]=[C:6]([OH:12])[CH:7]=[N:8][C:9]=1[S:10][CH3:11].Cl[CH:14]([F:16])[F:15]>O1CCOCC1.O.CCOCC>[F:15][CH:14]([F:16])[O:12][C:6]1[CH:5]=[C:4]([CH3:3])[C:9]([S:10][CH3:11])=[N:8][CH:7]=1

Participants

7

Reactant 3

HCID 6372ChlorodifluoromethaneHCID 14798Sodium HydroxideHCID 68856339HCID 68856339, compound

Product 1

HCID 68857309HCID 68857309, compoundYield 61%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

Solid sodium hydroxide (9.3 g, 232 mmol) were added in one portion to a stirred solution of 5-methyl-6-methylsulfanylpyridine-3-ol (7.2 g, 46.4 mmol) in 1,4-dioxane (75 mL) and water (25 mL) causing an exotherm to 50° C. Chlorodifluoromethane (13 g, 150 mmol) was then rapidly bubbled into the reaction over 9 minutes, causing a gradual exotherm to 75° C. After the reaction had cooled to room temperature, it was diluted with ether (100 mL) and water (100 mL) and the layers separated. The organic phase was extracted with water (6×100 mL), brine and dried (Na2SO4). Filtration and removal of solvent left a brown oil, 8.3 g, that was purified by chromatography on silica, eluting with 1:1 methylene chloride/hexanes to give product, as an orange liquid, 5.8 g, 28.3 mmol, 61 percent yield.

Workup

  1. customto 50° C
  2. customto 75° C
  3. customthe layers separated
  4. extractionThe organic phase was extracted with water (6×100 mL), brine
  5. dry with materialdried (Na2SO4)
  6. filtrationFiltration and removal of solvent
  7. waitleft a brown oil, 8.3 g, that
  8. customwas purified by chromatography on silica
  9. washeluting with 1:1 methylene chloride/hexanes
  10. customto give product

Sources & evidence

ORD record
ord-a7cb2f8a219e44b99fb190a2a41d0d82
Source dataset
uspto-grants-2009_05
Patent number
US07531482B2

Reaction notes

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