Iodine → 4-Hydroxy-3-iodobenzonitrile

Temperature

25 °C

In a 2000 mL round-bottom flask containing 10.0 g (84 mmol) of 4-cyanophenol, 450 mL conc. ammonium hydroxide was added and contents were allowed to stir at 25° C. for 15 min. Next, a solution of 67.9 g (409 mmol) potassium iodide and 21.3 g (84 mmol) iodine chips, dissolved in 100 mL water, was quickly added. The reaction mixture was allowed to stir at 25° C. for 18 h at which time contents were filtered. The filtrate was concentrated under reduced pressure and redissolved in 500 mL dichloromethane. The organic layer was then washed twice with 250 mL water, dried, and concentrated under reduced pressure to provide the title compound as a light yellow solid (14.3 g, 67% yield). 1HNMR (300 MHz, CDCl3) δ 7.03 (d, 1H), 7.66 (dd, 1H), 7.98 (s, 1H); MS DCI m/e, 263 (M+NH4)+.

1. additionwas added
2. additionwas quickly added
3. stirringto stir at 25° C. for 18 h at which time contents
4. filtrationwere filtered
5. concentrationThe filtrate was concentrated under reduced pressure
6. dissolutionredissolved in 500 mL dichloromethane
7. washThe organic layer was then washed twice with 250 mL water
8. customdried
9. concentrationconcentrated under reduced pressure

ORD record

ord-0eab3f3bc22d4489ac96370e2b8f1852

Source dataset

uspto-grants-2009_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07538138B2