3-Fluoro-4-(trifluoromethyl)benzaldehyde → (NE,S)-N-[[3-fluoro-4-(trifluoromethyl)phenyl]methylidene]-2-methylpropane-2-sulfinamide

HRID 2370762Notes

Reaction equation

HRID 2370762 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[C:10]([F:13])([F:12])[F:11])[CH:5]=O.[CH3:14][C:15]([S@@:18]([NH2:20])=[O:19])([CH3:17])[CH3:16]>C(Cl)Cl.S([O-])([O-])(=O)=O.[Cu+2]>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[C:10]([F:13])([F:12])[F:11])/[CH:5]=[N:20]/[S@:18]([C:15]([CH3:17])([CH3:16])[CH3:14])=[O:19]

Participants

5

Reactant 2

HCID 27375373-Fluoro-4-(trifluoromethyl)benzaldehydeHCID 11355477tert-Butylsulfinamide, (S)-(-)-

Product 1

HCID 89310589(NE,S)-N-[[3-fluoro-4-(trifluoromethyl)phenyl]methylidene]-2-methylpropane-2-sulfinamide

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-fluoro-4-(trifluoromethyl)benzaldehyde (5.7 g, 29.7 mmol) in DCM (60 mL) was added (S)-2-methylpropane-2-sulfinamide (7.19 g, 59.3 mmol) and copper (II) sulfate (18.94 g, 119 mmol). The suspension was stirred at rt under N2 for 20 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 (120 g, SiO2, 10-50% EtOAc/hexanes) to give (S,E)-N-(3-fluoro-4-(trifluoromethyl)benzylidene)-2-methylpropane-2-sulfinamide as a white 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 (120 g, SiO2, 10-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-f75cb5a45aee4b2dbd0bd1efb5c7a54c
Source dataset
uspto-grants-2014_04
Patent number
US08710043B2

Reaction notes

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