Benzofuran → 2-(3-Chloropropyl)benzofuran

Temperature

-15 °C

n-BuLi in heptanes (1.5 ml, 2.4 mmol, 1.6M) was added drop wise to benzofuran (236 mg, 2.0 mmol) in THF (5 ml) at −20° C. under argon. The reaction mixture was stirred at −15° C. for 30 min, then 1-chloro-3-iodopropane (322 μl, 3.0 mmol) and copper (I) iodide (38 mg, 0.2 mmol) were added. The reaction was stirred at −15° C. for 1 h, then NH4Cl (sat. aq., 5 ml) was added. The product was extracted with diethyl ether (2×30 ml) and the organic layer was washed with brine (10 ml), dried (K2CO3), filtered and concentrated in vacuo. The product was purified by column chromatography (0-1% diethyl ether in heptanes) to give 2-(3-chloro-propyl)-benzofuran (101 mg, 26%). 1H NMR (CDCl3): δ2.23 (tt, 2H), 2.97 (dt, 2H), 3.62 (t, 2H), 6.45 (q, 1H), 7.21 (m, 2H), 7.42 (m, 1H), 7.50 (m, 1H).

1. stirringThe reaction was stirred at −15° C. for 1 h
2. extractionThe product was extracted with diethyl ether (2×30 ml)
3. washthe organic layer was washed with brine (10 ml)
4. dry with materialdried (K2CO3)
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe product was purified by column chromatography (0-1% diethyl ether in heptanes)

ORD record

ord-c25b9abe160e480093cbb985c539ed87

Source dataset

uspto-grants-2003_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06627645B2