Imidazole → 1-(Benzyloxy)-3,4-difluoro-2-(2-iodoethyl)benzene

Participants

Reaction Conditions

Reaction Steps

A solution of Ph3P (697 mg, 2.66 mmol) and imidazole (181 mg, 2.66 mmol) in DCM (15 mL) was cooled to 0° C. Added to this was iodine (674 mg, 2.66 mmol) and the resulting mixture was stirred at 0° C. for 30 min. 2-(6-(benzyloxy)-2,3-difluorophenyl)ethanol (585 mg, 2.214 mmol) was added portionwise over several minutes and the resulting mixture was stirred at room temp. After 5 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) to give 1-(benzyloxy)-3,4-difluoro-2-(2-iodoethyl)benzene (720 mg, 1.924 mmol, 87% yield) as colorless oil. 1H NMR (500 MHz, CDCl3) δ 7.52-7.35 (m, 5H), 7.03 (q, J=9.3 Hz, 1H), 6.69-6.52 (m, 1H), 5.10 (s, 2H), 3.37-3.29 (m, 4H).

Provenance & Evidence