Iodoethane → 1,2-Difluoro-4-ethylsulfonylbenzene

HRID 1820797Notes

Reaction equation

HRID 1820797 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-2afca82b88f642d08ee2f4aefd96df3a
Source dataset
uspto-grants-2009_10
Patent number
US07605163B2

Reaction notes

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