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-3add077b7d2d471e92c369c89c8343fa

Source dataset

uspto-grants-1999_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06008217