Iodine → 2-Bromo-6-iodo-4-methylphenol

Temperatur

60 °C

2-Bromo-4-methylphenol (10.11 gm, 54.05 mmol) was mixed with concentrated ammonium hydroxide (50 ml) and methanol (20 ml). Potassium iodide (17.94 g, 108 mmol), iodine (13.72 g, 54.05 mmol) and water (60 ml) were mixed to give a dark brown solution which was added in portions to the phenol solution. Additional methanol (200 ml) was added in portions as precipitating product made the mixture too viscous to stir. When all the iodine solution had been added the mixture was heated to 60° C. till the brown color faded. The mixture was cooled, filtered and the solid rinsed three times with water. The solid was dissolved in dichloromethane, dried over magnesium sulfate, filtered and stripped to give 2-Bromo-4-methyl-6-iodophenol as an oil that crystallized on standing. The filtrate and water rinses were concentrated and extracted twice with ethyl acetate, dried over magnesium sulfate, filtered and stripped to give additional 2-bromo-4-methyl-6-iodophenol for a total of 16.24 g, 96% yield.

1. customto give a dark brown solution which
2. customas precipitating product
3. additionWhen all the iodine solution had been added the mixture
4. temperatureThe mixture was cooled
5. filtrationfiltered
6. washthe solid rinsed three times with water
7. dissolutionThe solid was dissolved in dichloromethane
8. dry with materialdried over magnesium sulfate
9. filtrationfiltered

ORD-Eintrag

ord-46f8c0218ccc42b981649fe9bb0f79e4

Quelldatensatz

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07741326B2