Sodium borohydride → 6-Chloro-1-benzofuran

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).

1. customas monitored by TLC (1 h)
2. customThe reaction mixture was quenched by the addition of acetone (10 mL)
3. additionThis mixture was then treated with HCl (3N, 20 mL)
4. extractionthe resulting solution was extracted with ethyl acetate (3×50 mL)
5. dry with materialdried over anhydrous magnesium sulfate
6. concentrationconcentrated under vacuum

ORD record

ord-5cbb7d53f4be4bbc958c035a623a485f

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08912188B2