4-Iodobenzaldehyde → HCID 88540451, compound

HRID 2370809Notes

Reaction equation

HRID 2370809 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-79c00339f32a4280a1055ee71e0755d2
Source dataset
uspto-grants-2014_04
Patent number
US08710043B2

Reaction notes

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