반응 #70617

반응 방정식

4-bromo-N-tert-butyl-3-methylbenzenesulfonamide

DMF

→

N-tert-butyl-4-cyano-3-methylbenzenesulfonamide

용매

EtOAc

반응 조건

후처리

1. 1
   기타was purged with N2 for 20 min
2. 2
   workup.ADDITIONThen PdCl2(dppf) was added
3. 3
   기타no reaction
4. 4
   세척washed with 5% LiCl solution (2×)
5. 5
   건조The combined organic layers were dried (MgSO4)
6. 6
   농축concentrated
7. 7
   기타purified by silica gel column chromatography

실험 절차

A mixture of 4-bromo-N-tert-butyl-3-methylbenzenesulfonamide (1.207 g) and zinc cyanide (0.976 g) in DMF (8 ml) was purged with N2 for 20 min. Then PdCl2(dppf) was added. The reaction mixture was heated at 120° C. for 4 hours and showed no reaction. Pd(PPh3)4 was added and the reaction mixture was stirred at 120° C. over the weekend. The reaction mixture was diluted with EtOAc and washed with 5% LiCl solution (2×). The combined organic layers were dried (MgSO4), concentrated and purified by silica gel column chromatography to give 1.227 g N-tert-butyl-4-cyano-3-methylbenzenesulfonamide as a white solid.

출처