Dihydrobenzofuran → 3-Chloro-1-(2,3-dihydrobenzofuran-5-yl)propan-1-one

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Reaction Steps

To a solution of AlCl3 (2.22 g, 1.0 eq) in 50 mL CH2Cl2 was added 3-chloropropanoyl chloride (2.54 g, 1.2 eq) dropwise. The mixture was stirred at rt for 10 min, then 2,3-dihydrobenzofuran (2.0 g, 1.0 eq) was added. After stirring at rt overnight, the mixture was quenched with cold water and then extracted with CH2Cl2. The extract was dried over Na2SO4, filtered, the filtrate was concentrated and purified by column chromatography on silica gel to give the desired product (1.5 g, 62%). 1H NMR (400 MHz, CDCl3) δ 7.86 (s, 1H), 7.80 (d, J=8.4 Hz, 1H), 6.83 (d, J=8.4 Hz, 1H), 4.68 (t, J=8.8 Hz, 2H), 3.92 (t, J=6.8 Hz, 2H), 3.40 (t, J=8.8 Hz, 2H), 3.26 (t, J=6.8 Hz, 2H).

Provenance & Evidence