METHYL 2-AMINO-5-BROMO-3-IODOBENZOATE synthesis

Yield: 82%

Reaction Conditions:

with N-iodo-succinimide;acetic acid at 20; for 17 h;

Steps:

S9
Example S9; Preparation of 5-bromo-1H-indole-7-carboxylic acid; 371 mg of 2-amino-5-bromo-benzoic acid methyl ester (2 mmol) was dissolved in 2 ml conc acetic acid and treated with 495 mg of N-iodosuccinimide (2.2 mmol) at rt for 17 h. The reaction mixture was then poured on 5 ml saturated sodium bicarbonate solution and ice, extracted twice with EtOAc. The combined organic phases were then washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo, leading to 585 mg 2-amino-5-bromo-3-iodo-benzoic acid methyl ester (82%) as a light brown solid. MS (EI) 354.9 (M)⁺.

References:

Conte-Mayweg, Aurelia;Kuehne, Holger;Luebbers, Thomas;Maugeais, Cyrille;Mueller, Werner;Pflieger, Philippe US2006/30613, 2006, A1 Location in patent:Page/Page column 21-22