Sodium Iodide → N-(3-Iodophenyl)maleimide

Participants

Reaction Steps

To a stirred solution of sodium iodide (32 mg, 0.21 mmol) in H2O (100 μL), was added N-(m-tri-n-butylstannylphenyl)maleimide as described above (0.1 g, 0.21 mmol) in CH2Cl2 (2 mL), followed by a solution of chloramine-T (59 mg, 0.21 mmol) in H2O (2 mL). Reaction progress was followed by TLC on silica gel GHLFC plates (EtOAc/hexane, 1:3), starting material 4 Rf 0.65. The reaction mixture was stirred at room temperature for 30 minutes. The mixture initially turned yellow from the formation of I+. The solution rapidly became lighter until a colorless solution resulted. To this was added 2 mL of 5% aqueous sodium bisulfite and the resulting mixture was extracted with dichloromethane (4×10 mL). The dichloromethane extracts were dried (MgSO4), and the solvent was removed in vacuo to give the desired product N-(m-iodophenyl)maleimide (60 mg/ 95%): TLC (EtOAc/hexane, 1:3) Rf 0.42; mp 154°-155° C. 1H NMR (CDCl3), δ); 7.1-7.7 (multiplets, 4H, 4 aryl CH); 6.8 (singlet, 2H, 2 CHC=O).

Provenance & Evidence