Sodium Iodide → HCID 69036720, compound

HRID 1820802Notes

Reaction equation

HRID 1820802 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.Br[CH:20]1[CH2:23][CH2:22][CH2:21]1.[I-].[Na+]>CN(C=O)C>[CH:20]1([S:9]([C:4]2[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=2)(=[O:11])=[O:10])[CH2:23][CH2:22][CH2:21]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 78110BromocyclobutaneHCID 138368283,4-Difluoro-benzenesulfinic acid

Product 1

HCID 69036720HCID 69036720, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To 5.6 mmol 3,4-difluoro-benzenesulfinic acid and 6.2 mmol triethylamine in 10 ml DMF were added 8.4 mmol bromocyclobutane and 0.2 mmol sodium iodide and the mixture heated at 100° C. for 48 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. MS (m/e): 233.1 (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 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-a58fc05469794feb9767009e43252ae8
Source dataset
uspto-grants-2009_10
Patent number
US07605163B2

Reaction notes

Loading…