Diethyl Ether → 6-Iodo-2,3-dihydro-1,3-benzoxazol-2-one

Participants

Reaction Conditions

Reaction Steps

Crude 4-Iodosalicylic acid (1.0 g, 3.8 mmol) was dissolved in THF (28 mL) and Et3N (1.15 mL, 8.2 mmol). DPPA (1.7 mL, 7.8 mmol) was added. This was heated at 70° C. overnight. The reaction mixture was then partitioned between H2O and EtOAc. The organic layer was dried and concentrated. Purification by silica gel chromatography (9/1, CH2Cl2/EtOAc) yielded 472 mg crude intermediate. Trituration with ether yielded 6-iodo-3H-benzooxazol-2-one (369 mg, 37%) as a white solid.

Provenance & Evidence