(4-AMino-3-iodo-phenyl)-acetic acid ethyl ester synthesis

Yield:405267-73-4 90%

Reaction Conditions:

with N-iodo-succinimide in acetonitrile;Reflux;Inert atmosphere;

Steps:

1 Synthesis of ethyl 2-(4-amino-3-iodophenyl)acetate (41)

To a solution of ethyl 2-(4-aminophenyl)acetate (10.00 g, 55.80 mmol) in acetonitrile (100 mL) was added N-iodosuccinimide (15.06 g, 66.94 mmol) at room temperature. The resulting mixture was refluxed overnight under a nitrogen atmosphere. After cooling down to room temperature, the resulting mixture was concentrated and the residue was purified by column chromatography on silica gel (1% to 20% ethyl acetate in petroleum ether). The fractions containing the desired product were collected and concentrated under reduced pressure to afford ethyl 2-(4-amino-3-iodophenyl)acetate (41) as a light yellow oil.[00400] Yield 15.31 g (90%).¹H NMR (400 MHz, DMSO) δ 7.45 (s, 1H), 6.97 (d, J=8.2 Hz, 1H), 6.70 (d, J=8.2 Hz, 1H), 5.13 (br s, 2H), 4.05 (t, J=7.2 Hz, 2H), 3.45 (s, 2H), 1.18 (t, J=7.2 Hz, 3H). m/z: [ESI⁺] 306 (M+H)⁺.

References:

WO2021/154902,2021,A1 Location in patent:Paragraph 00399-00400