4-Bromobenzaldehyde → HCID 12171907, compound

HRID 877347Notes

Reaction equation

HRID 877347 reaction equation
[Br: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]>[Br: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 707414-BromobenzaldehydeHCID 11355477tert-Butylsulfinamide, (S)-(-)-

Product 1

HCID 12171907HCID 12171907, compoundYield 97.2%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2.0 g (10 mmol) 4-bromobenzaldehyde in 20 ml CH2Cl2 at rt was added 1.3 g (10 mmol) (S)-(−)-2-methylpropane-2-sulfinamide and 2.4 g (10 mmol) copper (II) sulfate. After 24 h at room temperature, the reaction mixture was filtered through celite and concentrated in vacuo. Purification by flash chromatography (silica gel, linear gradient 0-40% EtOAc:hexane) afforded 2.8 g (90%) N-[(1E)-(4-bromophenyl)methylidene]-2-methylpropane-2-sulfinamide. ES-MS [M+1]=289.0.

Workup

  1. filtrationthe reaction mixture was filtered through celite and
  2. concentrationconcentrated in vacuo
  3. customPurification by flash chromatography (silica gel, linear gradient 0-40% EtOAc:hexane)

Sources & evidence

ORD record
ord-31c35f75f9f7402c874a50bfea0389bc
Source dataset
uspto-grants-2015_03
Patent number
US08987310B2

Reaction notes

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