Reaktion #47178

Reaktionsgleichung

phenylacetylene

N-(2-Benzoyl-4-chloro-phenyl)-4-bromo-benzenesulfonamide

dichloromethane

DME

→

N-(2-Benzoyl-4-chloro-phenyl)-4-phenylethynyl-benzenesulfonamide

Lösungsmittel

triethylamine

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONThe reaction was worked up by addition
2. 2
   Sonstigeto crushed ice
3. 3
   Extraktionextracted with ethyl acetate (3×75 mL)
4. 4
   Trocknenthe organic layer was dried (MgSO4)
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated
7. 7
   SonstigeThe crude product was chromatographed on silica gel using 10-30% EtOAc/Hexane

Vorschrift

To a magnetically stirred mixture of the N-(2-Benzoyl-4-chloro-phenyl)-4-bromo-benzenesulfonamide (450 mg, 1.0 mmol), [1,1′ Bis-(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (1:1) (30 mg, 0.037 mmol) and copper (I) iodide (100 mg, 0.52 mmol) was added DME (6 mL) and dry triethylamine (3 mL) under dry nitrogen. To this stirred mixture was added tetrabutylammonium iodide (250 mg), followed by the addition of phenylacetylene (0.240 mL). The dark green mixture was stirred at ambient temp overnight. The reaction was worked up by addition to crushed ice and extracted with ethyl acetate (3×75 mL), and the organic layer was dried (MgSO4), filtered and concentrated. The crude product was chromatographed on silica gel using 10-30% EtOAc/Hexane. 1H NMR (CDCl3) δ 9.64 (br s, 1H, NH), 7.75 (d, 1H. J=Hz), 7.75 (d, 1H, J=8.8 Hz), 7.48 (m, 8H), 7.36 (m, 7H). MS: m/z 472 (M+1)

Quelle