methyl 2-(4-amino-3-iodophenyl)acetate

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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). 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 concentrated The residue was purified by column chromatograph

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The crude (4-amino-3-iodophenyl)acetic acid (about 40 g, about 171 mmol) in methanol (110 mL) was added 100 mL of 4 M MeOH/HCl and the solution was stirred at ambient temperature over night. Distilled the solution under reduce pressure, and the residue was purified by silica gel cloumn chromatography to give methyl (4-amino-3-iodophenyl)acetate. 1H-NMR (300 MHz, CDCl3) δ ppm 7.54 (s, 1H), 7.04 (d, J=7.9 Hz, 1H), 6.68 (d, J=7.9 Hz, 1H), 3.67 (s, 3H), 3.46 (s, 2H). Distilled the solution the residue was purified by silica gel cloumn chromatography