Sodium Iodide → HCID 86711830, compound

HRID 623741Notes

Reaction equation

HRID 623741 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH2:9])=[C:4]([F:10])[CH:3]=1.[C:11]1([CH3:20])[CH:16]=[CH:15][C:14]([S:17]([O-:19])=[O:18])=[CH:13][CH:12]=1.[Na+].[Na+].[I-:23]>CC#N>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([I:23])[CH2:9][S:17]([C:14]2[CH:15]=[CH:16][C:11]([CH3:20])=[CH:12][CH:13]=2)(=[O:19])=[O:18])=[C:4]([F:10])[CH:3]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 2723791Sodium p-toluenesulfinateHCID 21617990HCID 21617990, compound

Product 1

HCID 86711830HCID 86711830, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mechanically stirred mixture of impure 4-chloro-2-fluoro-1-vinylbenzene (26.76 g, 154 mmol), sodium p-toluenesulfinate (28.8 g, 161 mmol) and NaI (34.6 g, 231 mmol) in MeCN (700 mL) was added (NH4)2Ce(NO3)6 (169 g, 308 mmol) portionwise. The mixture was stirred under a nitrogen atmosphere during 3 h at room temperature. The liquid was separated by decantation and the solids were washed with MeCN (3×100 mL). The solvent was evaporated in vacuo and re-dissolved in EtOAc (500 mL). The organic layer was washed with brine (400 mL), aqueous 10 wt % Na2S2O3 (2×200 mL) and brine (200 mL). The organic layer was dried (Na2SO4) and the solvent was evaporated to arrive at 51.86 g of crude title compound as a yellow solid.

Workup

  1. customThe liquid was separated by decantation
  2. washthe solids were washed with MeCN (3×100 mL)
  3. customThe solvent was evaporated in vacuo
  4. dissolutionre-dissolved in EtOAc (500 mL)
  5. washThe organic layer was washed with brine (400 mL), aqueous 10 wt % Na2S2O3 (2×200 mL) and brine (200 mL)
  6. dry with materialThe organic layer was dried (Na2SO4)
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-f264c77bf6bd40beaebf079931deafe8
Source dataset
uspto-grants-2016_04
Patent number
US09302988B2

Reaction notes

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