Ethyl orthoformate → methyl [3-iodo-4-(1H-tetrazol-1-yl)phenyl]acetate

Participants

Reaction Conditions

Reaction Steps

A solution of methyl (4-amino-3-iodophenyl)acetate (5 g, 17.2 mmol) and triethyl orthoformate (7.6 mg, 51.5 mmol) in 40 mL of HOAc was added sodium azide (1.2 g, 17.2 mmol), and the mixture was heated to 100° C. for 3 hours. The reaction mixture was cooled to ambient temperature. The solvent was removed under vacuum. The residue was dissolved in EtOAc, washed with water, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by column chromatograph to afford methyl [3-iodo-4-(1H-tetrazol-1-yl)phenyl]acetate. 1H-NMR (300 MHz, CDCl3) δ ppm 8.90 (s, 1H), 7.96 (s, 1H), 7.47 (d, J=8.2 Hz, 1H), 7.38 (d, J=7.9 Hz, 1H), 3.74 (s, 3H), 3.70 (s, 2H).

Provenance & Evidence