Pyridine → 3-Chloro-4-phenylfuran-2,5-dione

Participants

Reaction Conditions

Reaction Steps

To an ice cold solution of phenylmaleic anhydride (5.74 mmol, 1.0 g) in thionyl chloride (6.0 mL) was added drop wise pyridine (11.4 mmol, 0.9 g). The reaction mixture was stirred for 60 min at 0° C., followed by heating to 75° C. for 20 min. The reaction mixture was cooled to room temperature and the thionyl chloride was removed in vacuo. The crude residue was suspended in toluene (10 mL), refluxed for 10 min., followed by filtration of the hot mixture. The filtrate was concentrated to give 1.15 g (96%) of the title. 1H NMR (400 MHz, CDCl3) δ 8.05-8.00 (m, 2H), 7.59-7.51 (m, 3H).

Provenance & Evidence