Isopropyl iodide → 1,2,3-Trifluoro-4-(propane-2-sulfonyl)-benzene

HRID 1820806Notes

Reaction equation

HRID 1820806 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[CH:5]=[CH:4][C:3]=1[S:10]([OH:12])=[O:11].C(N(CC)CC)C.I[CH:21]([CH3:23])[CH3:22]>CN(C=O)C>[F:9][C:6]1[CH:5]=[CH:4][C:3]([S:10]([CH:21]([CH3:23])[CH3:22])(=[O:12])=[O:11])=[C:2]([F:1])[C:7]=1[F:8]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 8471TriethylamineHCID 50998774HCID 50998774, compound

Product 1

HCID 690368531,2,3-Trifluoro-4-(propane-2-sulfonyl)-benzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 20.4 mmol 2,3,4-trifluoro-benzenesulfinic acid (prepared in analogy to example 2.20(a) from 2,3,4-trifluoro-benzenesulfonyl chloride) and 61.2 mmol triethylamine in 20 ml DMF was added 40.8 mmol 2-iodopropane, and the mixture stirred at room temperature for 16 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 1:4) to afford the title compound.

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 1:4)

Sources & evidence

ORD record
ord-f385eaf9fde74d5db87bddecbe2ad143
Source dataset
uspto-grants-2009_10
Patent number
US07605163B2

Reaction notes

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