Phosgene → 8-fluoro-6-iodo-1H-benzo[d][1,3]oxazine-2,4-dione

Participants

Reaction Steps

To a solution of 500 mg (1.78 mmol) of 2-amino-3-fluoro-5-iodo-benzoic acid in 5.0 mL tetrahydrofuran was added 1.4 mL (2.67 mmol) of 20% w/v solution of phosgene in toluene. The reaction was stirred for 16 hours at room temperature. The solution was concentrated to dryness to afford 550 mg (1.79 mmol, quantitative yield) of 8-fluoro-6-iodo-1H-benzo[d][1,3]oxazine-2,4-dione as a brown powder. 1H NMR (500 MHz, DMSO-d6) δ 12.05 (s, 1H), 8.09 (dd, 1H), 7.98 (s, 1H).

Provenance & Evidence