4-Iodobenzaldehyde → HCID 88540451, compound

HRID 509371Notes

Reaction equation

HRID 509371 reaction equation
[I:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[CH3:10][C:11]([S:14]([NH2:16])=[O:15])([CH3:13])[CH3:12]>C(Cl)Cl.S([O-])([O-])(=O)=O.[Cu+2]>[I:1][C:2]1[CH:9]=[CH:8][C:5](/[CH:6]=[N:16]/[S:14]([C:11]([CH3:13])([CH3:12])[CH3:10])=[O:15])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 966574-IodobenzaldehydeHCID 3382465Tert-Butanesulfinamide

Product 1

HCID 88540451HCID 88540451, compound

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(iodo)benzaldehyde (2.00 g, 8.62 mmol) (BioNet Research) in DCM (20 mL) was added 2-methylpropane-2-sulfinamide (2.09 g, 17.2 mmol) (AK Scientific) and copper (II) sulfate (2.75 g, 17.2 mmol) (Fluka). The suspension was stirred at rt under N2 for 17 h. The suspension was then filtered through Celite® brand filter agent, and the solids were washed with DCM (2×20 mL). The filtrates were concentrated and purified by ISCO (80 g, SiO2, 0-100% EtOAc/hexanes) to give the title compound as a yellow solid.

Workup

  1. filtrationThe suspension was then filtered through Celite® brand
  2. filtrationfilter agent
  3. washthe solids were washed with DCM (2×20 mL)
  4. concentrationThe filtrates were concentrated
  5. custompurified by ISCO (80 g, SiO2, 0-100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-2f98511d3c264467a03f7f6fca80feb1
Source dataset
uspto-grants-2015_08
Patent number
US09096527B2

Reaction notes

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