HCID 56971745, compound → 2-Fluoro-4-methylsulfonylphenol

HRID 1931560Notes

Reaction equation

HRID 1931560 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[O:12]C>Br.C(O)(=O)C>[F:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:9])=[O:10])[CH:5]=[CH:4][C:3]=1[OH:12]

Participants

4

Reactant 1

HCID 56971745HCID 56971745, compound

Product 1

HCID 161288422-Fluoro-4-methylsulfonylphenolYield 86%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent2×

Procedure

A solution of 2-fluoro-4-methanesulfonyl-1-methoxy-benzene (1.00 g, 4.9 mmol) in a mixture of 48% aqueous HBr (3 mL) and 33% HBr in acetic acid (1.5 mL) was heated at reflux for 20 h. The reaction mixture was cooled to room temperature and extracted with ethyl acetate. The organic layer was dried (sodium sulfate), filtered, evaporated and chromatographed, eluting with 30% ethyl acetate/hexanes, to give 2-fluoro-4-methanesulfonyl-phenol (800 mg, 86%) as a white solid. Mass spectrum (APCI) m/z M−H=189.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 20 h
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried (sodium sulfate)
  5. filtrationfiltered
  6. customevaporated
  7. customchromatographed
  8. washeluting with 30% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-fe3a017c14a149c7af3d4314ab180f67
Source dataset
uspto-grants-2012_05
Patent number
US08188098B2

Reaction notes

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