Iodoethane → 1,2-Difluoro-4-ethylsulfonylbenzene

HRID 2251252Notes

Reaction equation

HRID 2251252 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:9]([OH:11])=[O:10])[CH:5]=[CH:6][C:7]=1[F:8].[CH2:12](N(CC)CC)[CH3:13].ICC>CN(C=O)C>[CH2:12]([S:9]([C:4]1[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=1)(=[O:11])=[O:10])[CH3:13]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 8471TriethylamineHCID 13836828HCID 13836828, compound

Product 1

HCID 265973661,2-Difluoro-4-ethylsulfonylbenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To 3.0 mmol 3,4-difluoro-benzenesulfinic acid and 3.0 mmol triethylamine in 10 ml DMF was added 7.5 mmol iodoethane and the mixture heated at 90° C. for 9 h. The reaction mixture was then poured onto water and extracted three times with ethyl acetate. The combined organic phases were then washed twice with saturated aq. NaCl solution, dried over Na2SO4, and concentrated in vacuo. The residue was chromatographed on silica gel (eluant: ethyl acetate/heptane 1:7) to afford the title compound. MS (m/e): 206.9 (M+H+, 100%)

Workup

  1. additionThe reaction mixture was then poured onto water
  2. extractionextracted three times with ethyl acetate
  3. washThe combined organic phases were then washed twice with saturated aq. NaCl solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on silica gel (eluant: ethyl acetate/heptane 1:7)

Sources & evidence

ORD record
ord-4935fef6bc654594b0b463654c0090dc
Source dataset
uspto-grants-2008_01
Patent number
US07319099B2

Reaction notes

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