Reaktion #68558

ord-4f79440e739e4ef3b2297af9766d349c

Reaktionsgleichung

O=Cc1ccc(Br)cc1Cl
4-bromo-2-chlorobenzaldehyde
CC(C)(C)[S@](N)=O
(r)-(+)-2-methyl-2-propanesulfinamide
→
CC(C)(C)[S@@](=O)/N=C\c1ccc(Br)cc1Cl
(R,Z)—N-(4-bromo-2-chlorobenzylidene)-2-methylpropane-2-sulfinamide

Edukte

O=Cc1ccc(Br)cc1Cl
4-bromo-2-chlorobenzaldehyde
CC(C)(C)[S@](N)=O
(r)-(+)-2-methyl-2-propanesulfinamide

Reagenzien

O=S(=O)([O-])[O-].[Cu+2]
copper(ii) sulfate

Lösungsmittel

ClCCl
DCM

Reaktionsbedingungen

Temperatur
37°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeReaction
  2. 2
    Filtrationfiltered through Celite, and solid
  3. 3
    Waschenwashed repeatedly with DCM
  4. 4
    EinengenFiltrate concentrated
  5. 5
    Sonstigethen purified on silica (80 g)
  6. 6
    Wascheneluting product with 0>30% of EtOAc/Hex

Vorschrift

A suspension of 4-bromo-2-chlorobenzaldehyde (1150 mg, 5240 μmol), (r)-(+)-2-methyl-2-propanesulfinamide (1588 mg, 13100 μmol), copper(ii) sulfate (696.4 μl, 15720 μmol) in DCM (10 mL) was stirred at 37° C. for 78 h. Reaction filtered through Celite, and solid washed repeatedly with DCM. Filtrate concentrated then purified on silica (80 g) eluting product with 0>30% of EtOAc/Hex. MS (ESI pos. ion) m/z: 322/324 (MH+). Calc'd exact mass for C11H13BrClNOS: 321/323.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08524900B2uspto-grants-2013_09