Sodium Bicarbonate → 3-Fluoro-4-(methylsulfonyl)phenol

HRID 1931564Notes

Reaction equation

HRID 1931564 reaction equation
O[O:2][S:3]([O-:5])=O.[K+].[F:7][C:8]1[CH:9]=[C:10]([OH:16])[CH:11]=[CH:12][C:13]=1SC.[C:17](=O)(O)[O-].[Na+]>O.O1CCCC1>[F:7][C:8]1[CH:9]=[C:10]([OH:16])[CH:11]=[CH:12][C:13]=1[S:3]([CH3:17])(=[O:5])=[O:2]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 219046773-Fluoro-4-(methylthio)phenolHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 231456203-Fluoro-4-(methylsulfonyl)phenolYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of oxone (19.6 g, 32 mmol) in water (50 mL) was added to a rapidly stirred solution of 3-fluoro-4-methylsulfanyl-phenol (2.47 g, 15.6 mmol) in tetrahydrofuran (100 mL). The mixture was stirred for 1 h at room temperature and then it was poured into aqueous sodium bicarbonate solution. The mixture was extracted three times with ethyl acetate, and the combined extracts were washed with brine, dried (magnesium sulfate), filtered, evaporated, and eluted through a short silica plug with 50% ethyl acetate/hexanes to give 3-fluoro-4-methanesulfonyl-phenol (2.31 g, 78%) as a light brown oil that solidified on standing.

Workup

  1. extractionThe mixture was extracted three times with ethyl acetate
  2. washthe combined extracts were washed with brine
  3. dry with materialdried (magnesium sulfate)
  4. filtrationfiltered
  5. customevaporated
  6. washeluted through a short silica plug with 50% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-6d4ef4476b57481e9dcdfdb9eafdfb72
Source dataset
uspto-grants-2012_05
Patent number
US08188098B2

Reaction notes

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