Sulfuric Acid → 1-(2-Hydroxy-3-iodophenyl)ethan-1-one

Temperature

0 °C

A suspension of 3'-amino-2'-hydroxyacetophenone hydrobromide (2.5 g, 10.8 mmol) in water (10 ml) at 0° C. was added successively with concentrated sulfuric acid (0.70 ml) and sodium nitrite (0.783 g, 11.3 mmol) dissolved in water (1.5 ml) and the mixture was left under stirring at 0° C. for 20 min. After that, concentrated sulfuric acid (0.2 ml) was added and the resulting mixture was poured onto a solution of potassium iodide (2.2 g) in water (2 ml) cooled at 0° C. Copper powder (11 mg) was added in a few minutes and the mixture was left at 75° C. for 2 h. After this time the mixture was left to cool at room temperature, then extracted with chloroform (3×50 ml), the organic phase was washed with a 5% sodium thiosulfate solution, dried and the solvent was evaporated off under reduced pressure. The resulting residue was purified by column chromatography eluting with petroleum ether:chloroform, 6:4, thereby recovering 1.95 g of title compound (69% yield).

1. waitthe mixture was left
2. temperaturecooled at 0° C
3. waitthe mixture was left at 75° C. for 2 h
4. waitAfter this time the mixture was left
5. temperatureto cool at room temperature
6. extractionextracted with chloroform (3×50 ml)
7. washthe organic phase was washed with a 5% sodium thiosulfate solution
8. customdried
9. customthe solvent was evaporated off under reduced pressure
10. customThe resulting residue was purified by column chromatography
11. washeluting with petroleum ether

ORD record

ord-2643f69d5f4843ff92e3117d89f81fd7

Source dataset

uspto-grants-1999_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05990142