Cesium carbonate → 3-Iodo-5-methanesulfonyl-phenol

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

To a solution of syn-benzaldehyde oxime (3.71 g, 30.6 mmol) in DMF (80 mL) was added cesium carbonate (19.9 g, 61.3 mmol) and heated to 90° C. for 1-2 min before a solution of 1-iodo-3-methanesulfonyl-5-nitro-benzene (5.0 g, 15.3 mmol) in DMF (80 mL) was added. The resulting dark brown solution was stirred at 90° C. for 15 h. The reaction mixture was then cooled down and diluted with EtOAc and washed with 10% HCl. The organic phase was then washed again with brine. The combined organic extracts were dried over sodium sulfate and evaporated under reduced pressure to obtain a crude brown oil which was purified on ISCO column (330 g). The desired compound was eluted with 70% EtOAc-Hexanes. The desired fractions were combined and evaporated under reduced pressure to afford 2.5 g (55%) of 3-iodo-5-methanesulfonyl-phenol as an orange solid. HR-ES(+) m/e calcd for C7H7O3SI (M+H)+ 298.9234, found 298.9234.

Herkunft & Nachweise