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) δ7.34 (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-ebc847ec4f4c417780a76b267cde8b83

Source dataset

uspto-grants-1999_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05874424