6-bromo-1-benzofuran-3-one

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

Procedure: To a solution of 6-bromo-benzofuran-3-one (10.5 g, 49.28 mmol) in methanol (100 ml) was added NaBH4 (2.37 g, 64.07 mmol) at 0° C. The reaction mixture was then stirred for 2 hours at room temperature. It was subsequently quenched with saturated ammonium chloride solution (50 ml) and extracted twice with ethyl acetate (2×50 ml). The combined organic phases were dried over Na2SO4 and evaporated under reduced pressure to give 9.75 g (92%) of the title compound as colorless liquid. It was subsequently quenched with saturated ammonium chloride solution (50 ml) extracted twice with ethyl acetate (2×50 ml) The combined organic phases were dried over Na2SO4 evaporated under reduced pressure

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

Procedure: Sodium hydride (0.7 g, 0.0173 mol) was washed with hexanes then suspended in THF (8 mL). Diethyl cyanomethylphosphonate (3.07 g, 0.0173 mol) was added dropwise and stirred 10 minutes to give clear yellow solution. A solution of 11-5 (3.38 g, 0.0158 mol) in THF (20 mL) was added dropwise, the solution stirred for 0.5 hour, then heated to reflux for 0.5 hour. A solution of 6N HCL (3.4 mL) was added and the THF was removed under vacuum. The concentrated solution was diluted with Et2O and washed with 4×30 mL 6N HCl, the ether layer was dried (MgSO4), filtered and evaporated. The residue was chromatographed (20% EtOAc/Hexanes) to give 11-6 as an orange solid. to give clear yellow solution the solution stirred for 0.5 hour heated to reflux for 0.5 hour A solution of 6N HCL (3.4 mL) was added the THF was removed under vacuum The concentrated solution was diluted with Et2O washed with 4×30 mL 6N HCl the ether layer was dried (MgSO4) filtered evaporated The residue was chromatographed (20% EtOAc/Hexanes)