6-iodo-1-benzofuran-3-one

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Sodium hydride (37.3 g; 0.886 mol; 1.2 eq; 60 wt % dispersion in oil) was suspended in hexanes (120 mL) under N2. The sodium hydride was allowed to settle and the hexanes were syringed out of the flask and dry THF (100 mL) added. The NaH was washed again and the THF decanted. A fresh portion of dry THF (300 mL) was added and diethylcyanomethylphosphonate (0.886; 1.2 eq) was added drop wise over 35 min while keeping the temperature at 20-22° C. A solution of 6-iodo-1-benzofuran-3(2H)-one (192.0 g; 0.74 mol) in THF (1.75 L) then added over 35 min at 15-25° C. After 30 min stirring, 6N HCl (750 mL), MTBE (750 mL), and H2O (500 mL) were added. The layers were separated, sodium sulfate was added to the organic layer. The organics were filtered and concentrated. The resulting red solids were suspended in MTBE (500 mL), washed four times with 1N HCl (400 mL). The solvent was evaporated to afford 214 g of the title product. 1H-NMR (400 MHz, CDCl3): δ 3.75 (bs, 1H), 7.34 (d, 1H), 7.60 (s, 1H), 7.62 (dd, 1H), 7.91 (d, 1H). added The NaH was washed again the THF decanted A fresh portion of dry THF (300 mL) was added at 20-22° C The layers were separated sodium sulfate was added to the organic layer The organics were filtered concentrated washed four times with 1N HCl (400 mL) The solvent was evaporated