Sodium Iodide → HCID 69036720, compound
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]1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
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
- additionThe reaction mixture was then poured onto water
- extractionextracted three times with ethyl acetate
- washThe combined organic phases were then washed with saturated aq. NaCl solution
- dry with materialdried over Na2SO4
- concentrationconcentrated in vacuo
- customThe residue was chromatographed on silica gel (eluant: ethyl acetate/heptane gradient)
Sources & evidence
- ORD record
- ord-7c433171b757440c90e576fd6e6d3d27
- Source dataset
- uspto-grants-2008_01
- Patent number
- US07319099B2
Reaction notes
Loading…