Imidazole → 2-Bromo-4-fluoro-1-(2-iodoethyl)-benzene

Participants

Reaction Conditions

Reaction Steps

A solution of Ph3P (2.57 g, 9.81 mmol) and imidazole (0.668 g, 9.81 mmol) in DCM (50 mL) was cooled to 0° C. Added to this was iodine (2.489 g, 9.81 mmol) and the resulting mixture was stirred at 0° C. for 30 min. 2-(2-Bromo-4-fluorophenyl)ethanol (1.79 g, 8.17 mmol) was added portionwise over several minutes and the resulting mixture was stirred at room temp. After 16 h, the mixture was filtered washing the solids with DCM. The filtrate was washed with aq Na2S2O3 and the organic phase was dried (Na2SO4), filtered and concentrated. The residue was purified by flash chromatography (Biotage; 0%-100% EtOAc/hexane; 20 CV) to give 2-bromo-4-fluoro-1-(2-iodoethyl)benzene (2.4 g, 7.30 mmol, 89% yield) as a colorless oil. 1H NMR (500 MHz, CDCl3) δ 7.33 (dd, J=8.2, 2.7 Hz, 1H), 7.25 (dd, J=8.5, 5.8 Hz, 1H), 7.02 (td, J=8.2, 2.6 Hz, 1H), 3.41-3.35 (m, 2H), 3.32-3.26 (m, 2H).

Provenance & Evidence