Water → 1,2-Difluoro-4-phenylsulfonylbenzene

HRID 1686403Notes

Reaction equation

HRID 1686403 reaction equation
[C:1]1([S:7][C:8]2[CH:13]=[CH:12][C:11]([F:14])=[C:10]([F:15])[CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH2:16].[OH:17]OS([O-])=O.[K+]>C(#N)C>[C:1]1([S:7]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[C:10]([F:15])[CH:9]=2)(=[O:17])=[O:16])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 23707502Potassium hydroxy sulfiteHCID 667340833,4-Difluorophenyl phenyl sulfide

Product 1

HCID 269861771,2-Difluoro-4-phenylsulfonylbenzene

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3,4-difluoroaniline (3.5 g), acetonitrile (60 ml), diphenyldisulfide (6 g) and isoamyl nitrite (8 ml) were charged to a flask and heated at 60° C. for 2 h then evaporated under reduced pressure. The residue was purified by flash column chromatography (eluent isohexane) to give the subtitle compound. The product (3,4-difluorophenyl phenyl sulfide) was dissolved in acetonitrile (60 ml). Water (10 ml) and oxone (20 g) were added and stirred for 72 h at RT. The reaction mixture was partitioned between ether/water, the organics were separated, washed with water, then dried (MgSO4) and evaporated under reduced pressure. The residue was purified by flash column chromatography (eluent 5-10% ethyl acetate/isohexane) to give the subtitle compound (2.14 g).

Workup

  1. customThe reaction mixture was partitioned between ether/water
  2. customthe organics were separated
  3. washwashed with water
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure
  6. customThe residue was purified by flash column chromatography (eluent 5-10% ethyl acetate/isohexane)

Sources & evidence

ORD record
ord-302f30126da6495984bc2f12ed333f21
Source dataset
uspto-grants-2012_04
Patent number
US08148572B2

Reaction notes

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