Sulfuric Acid → 5-Chloro-4-fluoro-2-iodophenol

N-iodosuccinimide (4.61 g, 20.5 mmol), was suspended in glacial acetic acid (20 ml). To this suspension was added 3-chloro-4-fluorophenol (3.0 g, 20.0 mmol) and then concentrated sulphuric acid (0.36 ml, 6.14 mmol) was added dropwise over 5 minutes. The resulting brown/orange suspension was stirred at room temperature for 18 hours. The mixture was concentrated in vacuo and the residue was partitioned between water and dichloromethane, the dichloromethane was dried over anhydrous magnesium sulphate, filtered and concentrated in vacuo to give an orange/red oil. The crude product was purified by column chromatography on silica gel using 1:1 ethyl acetate:heptane to give the title compound as a pale orange/brown solid (3.50 g, 60% yield)

1. concentrationThe mixture was concentrated in vacuo
2. customthe residue was partitioned between water and dichloromethane
3. dry with materialthe dichloromethane was dried over anhydrous magnesium sulphate
4. filtrationfiltered
5. concentrationconcentrated in vacuo
6. customto give an orange/red oil
7. customThe crude product was purified by column chromatography on silica gel using 1:1 ethyl acetate

ORD record

ord-47aa5001d19741338414b8a49739c320

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08541588B2