Water → 4-Chloro-5-hydroxy-1(3H)-isobenzofuranone

Participants

Reaction Conditions

Reaction Steps

To a flask charged with 4-bromo-2-chloro-3-(hydroxymethyl)phenol (2.44 g, 10.3 mmol) and a stir bar was added CuCN (2.76 g, 30.8 mmol) and DMF (25 mL). The flask was fitted with a condenser and purged three times with Nitrogen. The solution was then heated to 145° C. for 2 hours. At that point, water (0.555 mL, 30.8 mmol) was added to the reaction via a syringe, and the reaction was kept at 100° C. for another 24 hours. The reaction was cooled to RT, diluted with DCM (100 mL), and filtered through a pad of celite to remove the solids. The filtrate was washed with saturated NH4OAc, dried over sodium sulfate, concentrated and purified by silica gel flash chromatography. 4-Chloro-5-hydroxy-2-benzofuran-1(3H)-one was collected after removal of solvents. 1H-NMR (500 MHz, CDCl3) δ ppm 9.13 (broad, 1H), 7.68 (d, J=8.5 Hz, 1H), 7.19 (d, J=8.5 Hz, 1H), 5.23 (s, 2H).

Provenance & Evidence