Sodium Sulfite → 4-Chloro-2-(4-hydroxy-phenyl)-7-methoxy-benzofuran-5-ol

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Reaction Steps

Compound 62 (0.1 g, 0.39 mmol) in CH3CN (10 mL) was treated with portionwise addition of NCS (0.033 g, 0.24 mmol). After addition, 10% Na2SO3 aq was added followed by NaHCO3 and brine. The EtOAc layer was dried over MgSO4, filtered, concentrated and chromatographed on silica gel (3:7 EtOAc/hexanes) to yield 0.016 g of the product: Mp=176-177° C.; 1H NMR (DMSO-d6) δ 9.89 (br s, 2 H), 7.74 (d, 2 H, J=8.6 Hz), 7.10 (s, 1 H), 6.87 (d, 2 H, J=8.7 Hz), 6.55 (s, 1 H), 3.91 (s, 3 H); MS 291 (M+H)+.

Provenance & Evidence