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

Temperatur

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-Eintrag

ord-2643f69d5f4843ff92e3117d89f81fd7

Quelldatensatz

uspto-grants-1999_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05990142