Iodine → 2-(4-Amino-3-iodophenyl)ethanol

4-Aminophenethyl alcohol (9.60 g, 70 mmol, 1.0 eq) was added to a mixture of iodine (17.78 g, 70 mmol, 1.0 eq) and silver sulfate (21.83 g, 70 mmol, 1.0 eq) in anhydrous ethanol (200 mL) at room temperature. The reaction mixture was stirred under nitrogen for 1.5 hours. After stirring was stopped, the solid was removed by filtration. The filtrate was concentrated, and the residue was dissolved in dichloromethane (200 mL), and then washed with aqueous 5% NaOH solution (2×150 mL) and water (150 mL). The organic layer was dried over MgSO4, filtered and concentrated in vacuo to give a crude oil which was purified by flash chromatography (SiO2, hexanes-ethyl acetate) to yield 6.0 g of the desired ortho-iodo aniline as orange gel-like solid (32.4% yield).

1. stirringAfter stirring
2. customthe solid was removed by filtration
3. concentrationThe filtrate was concentrated
4. dissolutionthe residue was dissolved in dichloromethane (200 mL)
5. washwashed with aqueous 5% NaOH solution (2×150 mL) and water (150 mL)
6. dry with materialThe organic layer was dried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customto give a crude oil which
10. customwas purified by flash chromatography (SiO2, hexanes-ethyl acetate)

ORD record

ord-fcdf1696d9644c899dc80b4b35ef9592

Source dataset

uspto-grants-2005_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06951848B2