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ChemicalBook CAS DataBase List 5-CHLORO-2-IODOANISOLE

5-CHLORO-2-IODOANISOLE synthesis

6synthesis methods
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Yield: 88%

Reaction Conditions:

Stage #1:4-chloro-o-anisidine with sulfuric acid;sodium nitrite in water at 5; for 0.75 h;
Stage #2: with potassium iodide in water at 20;

Steps:

59.2 Step 2: Preparation of 4-chloro-1-iodo-2-methoxybenzene
1.45g of 4-chloro-2-methoxyaniline was dissolved in a solution of 60 ml of water and 10 ml of concentrated sulfuric acid and cooled to below 5 °C in an ice bath.
Further, 634 mg of sodium nitrite was dissolved in 1 ml of water and slowly added dropwise to the reaction solution, and the mixture was stirred under ice cooling for 45 minutes, and then 1.98 g of potassium iodide aqueous solution (5 ml) was added dropwise.
After stirred at room temperature for 1 hour, the mixture was extracted with EtOAc, washed with a saturated aqueous solution of sodium thiosulfate, dried over anhydrous sodium sulfate and then isolated by column chromatography (PE 100%) to obtain 2.17 g of liquid, yield 88%.

References:

Shanghai Institute of Materia Medica, Chinese Academy of Sciences;DUAN, Wenhu;GENG, Meiyu;WANG, Yuming;AI, Jing;FAN, Jun;DAI, Yang;DING, Jian EP3486244, 2019, A1 Location in patent:Paragraph 0376; 0377

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