6-bromo-2,3-dihydro-1-benzofuran-3-ol

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

Procedure: In analogy to the procedures described for the preparation of intermediates A-2 [B] and A-2 [C], (rac)-6-bromo-2,3-dihydro-benzofuran-3-ol was treated with diphenylphosphoryl azide, DBU in toluene to give (rac)-3-azido-6-bromo-2,3-dihydro-benzofuran, which was subsequently reduced with triphenylphosphine in THF/water to yield the title compound as light yellow oil. MS: 213 (M+, 1Br).

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