반응 #47178

반응 방정식

phenylacetylene

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

dichloromethane

DME

→

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

용매

triethylamine

반응 조건

후처리

1. 1
   workup.ADDITIONThe reaction was worked up by addition
2. 2
   기타to crushed ice
3. 3
   추출extracted with ethyl acetate (3×75 mL)
4. 4
   건조the organic layer was dried (MgSO4)
5. 5
   여과filtered
6. 6
   농축concentrated
7. 7
   기타The crude product was chromatographed on silica gel using 10-30% EtOAc/Hexane

실험 절차

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)

출처