Yield:-

Reaction Conditions:

Stage #1:5-bromo-2-iodo-benzoic acid with HATU in dichloromethane;N,N-dimethyl-formamide for 0.0333333 h;
Stage #2: with ammonium chloride in dichloromethane;N,N-dimethyl-formamide for 1 h;

Steps:

10.1 STEP 1.
STEP 1. Preparation of 5-Bromo-2-iodobenzamide HATU (25 g, 65.8 mmol) was added to 5-bromo-2-iodobenzoic acid (20 g, 61.2 mmol) in 1:1 mixture of CH₂Cl₂ and dimethylformamide (200 mL) and the solution stirred 2 min. Ammonium chloride (20 g) was added, and the heterogeneous mixture was stirred 1 h. Ammonium hydroxide (20 mL) was added. The solution was filtered, diluted with ethyl acetate, washed with water, 1 N HCl, saturated sodium bicarbonate, and saturated NaCl, dried (magnesium sulfate), filtered, and concentrated under reduced pressure to yield a white precipitate. The solid was filtered to provide 5-bromo-2-iodobenzamide (14.4 g). ESI MS m/z 327.0 [M+H]⁺.

References:

John, Varghese;Hom, Roy;Sealy, Jennifer;Tucker, John US2006/14737, 2006, A1 Location in patent:Page/Page column 32