Sodium Iodide → 1-Chloro-2-(iodomethyl)benzene

A mixture of 2-chlorophenylmethylbromide (4 g, 19.47 mmol) and NaI (14 g, 97.33 mmol) in acetone (40 ml) was stirred under reflux for 1 hour. The reaction mixture was cooled, filtered and concentrated in vacuo. The residue was triturated with hexane and filtered. The solution was concentrated in vacuo, and the resulting oil purified by flash chromatography (silica, hexane) to afford the title compound (4.67 g, 63%) as an oil: 1H NMR (CDCl3) δ 7.34 (4H, m), 4.54 (2H, s).

1. temperatureunder reflux for 1 hour
2. temperatureThe reaction mixture was cooled
3. filtrationfiltered
4. concentrationconcentrated in vacuo
5. customThe residue was triturated with hexane
6. filtrationfiltered
7. concentrationThe solution was concentrated in vacuo
8. customthe resulting oil purified by flash chromatography (silica, hexane)

ORD record

ord-6ff2b7dc67114b10ba23ea65d77a6904

Source dataset

uspto-grants-2001_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06258948B1