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ChemicalBook CAS DataBase List 2-Iodobenzoic acid
88-67-5

2-Iodobenzoic acid synthesis

12synthesis methods
2-Iodobenzoic acid, also known as o-iodobenzoic acid, is an important pharmaceutical chemical raw material and an intermediate for the synthesis of various periodic iodine reagents. It can be obtained by diazotization and replacement reaction of anthranilic acid.  Anthranilic acid with sodium nitrite in sulfuric acid diazotize at below 10°C, filter the diazo liquid, add a mixture of potassium iodide and sulfuric acid, stirred for 10 minutes, boil, filter, and washed with sodium thiosulfate solution , and then recrystallized with water to obtain 2-Iodobenzoic acid.
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Yield:88-67-5 77%

Reaction Conditions:

with [2,2]bipyridinyl;lithium hydroxide monohydrate;oxygen;sodium hydroxide at 50; under 760.051 Torr; for 10 h;Sealed tube;

Steps:

3.4. General Procedure for the Oxidation of Aldehyde 1

General procedure: Aldehyde 1 (0.2 mmol), Ag/C3N4 (10 mol%), NaOH (1 equiv), H2O (1 mL) were added into a 10 mL sealed tube under O2 (1 atm). The mixture was stirred at 50o C for 10 h. Then the reaction was stopped and 1M dilute hydrochloric acid was added to adjust the pH value to 3. The mixture was extracted with ethyl acetate (3 × 3 mL). The combined organic phase was dried with Na2SO4 and concentrated under reduced pressure. The residue was purified by flash column chromatography (5:1 hexanes and ethyl acetate).

References:

Wu, Chaolong;Yao, Xiaoquan;Yu, Min;Zhou, Li;Zhu, Li [Letters in Organic Chemistry,2021,vol. 18,# 3,p. 167 - 175]

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