Triethylamine → 3-Chloro-1,2-benzoxazole

Participants

Reaction Steps

2-Hydroxy benzisoxazole 11 (1.03 gr, 6.25 mmol), triethylarnine (632 mg, 6.25 mmol) and phosphorousoxychloride (1.92 gr, 12.5 mmol) were heated in a sealed tube at 150° C. for 18 h. After this time the reaction was cooled to room temperature and diluted with ether and carefully quenched with excess ice/water. The resulting mixture was stirred for 15 min then the organic layer was washed with water (2×), brine (1×), dried with magnesium sulfate, filtered and evaporated to afford 12 as a white solid after column chromatography (hexanes/ethyl acetate, 97:3); 1H-NMR (CDCl3, 500 MHz) δ 7.65-7.63 9 m, 2H), 7.42 (dd, 1H).

Provenance & Evidence