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-c36effaa1b6e4443ac4bd8583e688c94

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08907101B2