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

To a suspension of N-iodosuccinamide (6.1 g, 27.3 mmol) in glacial acetic acid (23 mL) was added 4-chloro-3-fluorophenol (4.0 g, 27.3 mmol) and after 5 minutes sulphuric acid was added (0.5 mL, 8.2 mmol) and the reaction mixture was left to stir at room temperature for 16 hours. The reaction was quenched by addition of water (30 mL) and the compound was extracted into dichloromethane (3×30 mL). The combined organic layers were washed with 10% sodium metabisulphite aqueous solution (2×20 mL), then saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulphate, filtered and evaporated in vacuo. The crude material was purified by flash column chromatography (silica, toluene) to afford the desired product as an oil (4.0 g, 54%).

1. waitthe reaction mixture was left
2. customThe reaction was quenched by addition of water (30 mL)
3. extractionthe compound was extracted into dichloromethane (3×30 mL)
4. washThe combined organic layers were washed with 10% sodium metabisulphite aqueous solution (2×20 mL)
5. dry with materialsaturated aqueous sodium chloride solution, dried over anhydrous magnesium sulphate
6. filtrationfiltered
7. customevaporated in vacuo
8. customThe crude material was purified by flash column chromatography (silica, toluene)

ORD record

ord-b46d071507b344d690a0831be6d00b34

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08541588B2