Triethylamine → 4-(3-Chloro-propane-1-sulfonyl)-1,2-difluoro-benzene

HRID 2251254Notes

Reaction equation

HRID 2251254 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].C(N(CC)CC)C.[Cl:19][CH2:20][CH2:21][CH2:22]I>CN(C=O)C>[Cl:19][CH2:20][CH2:21][CH2:22][S:9]([C:4]1[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=1)(=[O:11])=[O:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 813631-Chloro-3-iodopropaneHCID 13836828HCID 13836828, compound

Product 1

HCID 433451294-(3-Chloro-propane-1-sulfonyl)-1,2-difluoro-benzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 28.3 mmol 3,4-difluoro-benzenesulfinic acid and 36.8 mmol triethylamine in 100 ml DMF was added 70.7 mmol 1-chloro-3-iodopropane and the mixture stirred at RT for 1 h. The reaction mixture was then poured onto water and extracted three times with ethyl acetate. The combined organic phases were then washed with saturated aq. NaCl solution, dried over Na2SO4, and concentrated in vacuo. The residue was chromatographed on silica gel (eluant: ethyl acetate/heptane gradient) 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 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 gradient)

Sources & evidence

ORD record
ord-c49393c1733c46c5a3383ef19a0454df
Source dataset
uspto-grants-2008_01
Patent number
US07319099B2

Reaction notes

Loading…