Water → HCID 18533212, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-bromo-1,2-benzoxazolinone (5.0 g, 23 mmol) in DMF (11 mL) was added copper (I) cyanide (3.6 g, 39 mmol) and the reaction heated at 165° C. After 6.5 h, the reaction mixture was cooled to rt and water (20 mL) and sodium cyanide (3.6 g) were added and the reaction heated at 100° C. After 12 h, the reaction mixture was extracted with ethyl acetate and the combined organic layers were filtered through a scrub pad of silica gel eluting with ethyl acetate. The filtrate was concentrated under reduced pressure to give 1.9 g (51%) of 4-cyano-1,2-benzoxazolinone as a brown solid which required no further purification. 1H NMR (400 MHz, DMSO) δ 7.8 (s, 1H), 7.6 (d, 1H), 7.2 (d, 1H).

Provenance & Evidence