Sodium borohydride → 6-Chloro-1-benzofuran

Participants

Reaction Steps

To a solution of 6-chloro-2,3-dihydro-1-benzofuran-3-one (2.5 g, 14.83 mmol) in methanol (50 mL) was treated with NaBH4 (1.2 g, 31.58 mmol) in four equivalent portions at room temperature, until the reaction was complete, as monitored by TLC (1 h). The reaction mixture was quenched by the addition of acetone (10 mL). This mixture was then treated with HCl (3N, 20 mL). After stirring for another 1 h, the resulting solution was extracted with ethyl acetate (3×50 mL) dried over anhydrous magnesium sulfate and concentrated under vacuum to give 6-chloro-1-benzofuran as oil (2 g, crude).

Provenance & Evidence