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-Eintrag

ord-33b79d0d920e4f19a1599d3a9f86d1d3

Quelldatensatz

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08153814B2