Background and overview[1]
2-tert-butyl-4,6-diiodophenol can be used as a pharmaceutical synthesis intermediate. If 4-bromoquinoline-6-carboxylic acid is inhaled, move the patient to fresh air; if there is skin contact, take off contaminated clothing, rinse the skin thoroughly with soap and water, and seek medical attention if you feel unwell; if In case of eye contact, separate eyelids, rinse with running water or saline, and seek medical attention immediately; if ingested, rinse mouth immediately, do not induce vomiting, and seek medical attention immediately.
Preparation[1]
2-tert-butyl-4,6-diiodophenol was prepared as follows: 2-tert-butylphenol (99.95g, 665.36mmol) was dissolved in 1250mL methanol, and 31.96g (799.0mmol, 1.2 equivalent) was used Sodium hydroxide is converted to the corresponding phenolate by stirring the sodium hydroxide particles at room temperature and then cooling the reaction mixture in an ice/salt bath. Add sodium iodide (299.34g, 1997.07mmol, 3.0 equivalents) and 8.3% bleach (1265.83g, 1411.39mmol, 2.1 equivalents) into the cold reaction solution in four equal parts. Keep the reaction mixture <0 while adding the bleach. ℃. 500 mL of 20% (w/w) sodium thiosulfate solution was added over a period of 18 minutes while the temperature was increased from -0.6°C to 2.5°C. The pH of the reaction mixture was adjusted to approximately 3 by adding 197.5 mL of concentrated HCl over a period of 97 minutes while the reaction temperature was increased from 1.2°C to 4.1°C. The resulting slurry was filtered and the wet cake was washed with approximately 2 L of water. The wet filter cake was placed on a Buchner funnel under vacuum overnight (about 15 hours) to obtain 289.33g (efficiency adjusted yield = 254.61g) of the title product 2-tert-butyl-4,6-diiodophenol.
Apply[1]
2-tert-Butyl-4,6-diiodophenol can be used to prepare 1-tert-butyl-3,5-diiodo-2-methoxybenzene: The product 2-tert-butyl from Part A -4,6-Diiodophenol (93% assay, 21.6 g, 50 mmol) was dissolved in 140 mL acetone. Methyl iodide (4.2 mL, 67.5 mmol, 1.35 equiv) was added, followed by 50% aqueous sodium hydroxide (5.0 g, 62.5 mmol, 1.25 equiv). The reaction was stirred overnight and then concentrated to approximately 50-60 mL. 80 mL of heptanes was added, followed by 50 mL of water, and the layers were shaken and separated, and the aqueous layer was back-extracted with 20 mL of heptanes. The organic layers were combined and washed twice with 50 mL each of 10% aqueous NaCl to yield 91.1 g of a heptane solution, the content of which was determined to be 19.1 g of the title compound 1-tert-butyl-3,5-diiodo-2 -Methoxybenzene.
Main reference materials
[1] (CN104884440) Method for preparing antiviral compounds
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