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ChemicalBook CAS DataBase List 2-IODO-5-NITROBENZOIC ACID
19230-50-3

2-IODO-5-NITROBENZOIC ACID synthesis

9synthesis methods
2-Iodobenzoic acid

88-67-5

2-IODO-5-NITROBENZOIC ACID

19230-50-3

During this preparation, up to 25 mmol of I2 is generated. therefore, the synthesis operation must be carried out in a well-ventilated fume hood. The preparation was carried out with reference to the literature method [10]. 2-Iodobenzoic acid (4.10 g, 40.3 mmol, 1 equiv) was added to a mixed solution of HNO3 (35 mL, 65%) and H2SO4 (85 mL, 95%). The reaction mixture was heated to 135 °C and stirred at this temperature for 1 hour. Upon completion of the reaction, the resulting brown slurry was poured on ice, filtered to collect the gray precipitate, and washed with plenty of water. Subsequently, the filter cake was suspended in water (100 mL), heated to 100 °C and a solution consisting of KI (8.5 g, 51.2 mmol, 1.3 eq.) and H2SO4 (5 drops) dissolved in water (10 mL) was added in the process and the reaction was continued for 1 hour. Finally, the brown suspension was filtered while hot and washed with cold water to give the pure product 2-iodo-5-nitrobenzoic acid (5 g, 42% yield) as a brown solid. If the product is impure, it can be purified by boiling in water and then hot filtering.

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Yield:-

Steps:

Multi-step reaction with 2 steps
1: 80 percent / 1.) 5percent aq. NaOH; 2.) acetic acid / 6 h / Heating
2: 51 percent / NaNO2, KI,

References:

Katritzky, Alan R.;Duell, Bradley L.;Gallos, John K. [Magnetic Resonance in Chemistry,1989,vol. 27,# 11,p. 1007 - 1011]

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