Imidazole → 2-(Benzyloxy)-1,5-difluoro-3-(2-iodoethyl)benzene

Participants

Reaction Conditions

Reaction Steps

A solution of Ph3P (750 mg, 2.86 mmol) and imidazole (195 mg, 2.86 mmol) in DCM (15 mL) was cooled to 0° C. Added to this was iodine (726 mg, 2.86 mmol) and the resulting mixture was stirred at 0° C. for 30 min. Then, 2-(2-(benzyloxy)-3,5-difluorophenyl)ethanol (630 mg, 2.384 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 (5%-30% EtOAc/hexane) to give 2-(benzyloxy)-1,5-difluoro-3-(2-iodoethyl)benzene (630 mg, 1.684 mmol, 70.6% yield) as light yellow viscous oil. 1H NMR (500 MHz, CDCl3) δ 7.46-7.34 (m, 5H), 6.83 (ddd, J=11.3, 8.2, 3.0 Hz, 1H), 6.69 (dt, J=8.6, 2.3 Hz, 1H), 5.10 (s, 2H), 3.21 (d, J=7.7 Hz, 2H), 3.13-3.00 (m, 2H).

Provenance & Evidence