Imidazole → 1-(Benzyloxy)-4,5-difluoro-2-(2-iodoethyl)benzene

Temperature

0 °C

A solution of Ph3P (691 mg, 2.63 mmol) and imidazole (179 mg, 2.63 mmol) in DCM (15 mL) was cooled to 0° C. Added to this was iodine (668 mg, 2.63 mmol) and the resulting mixture was stirred at 0° C. for 30 min. 2-(2-(Benzyloxy)-4,5-difluorophenyl)ethanol (580 mg, 2.195 mmol) was added portionwise over several minutes and the resulting mixture was stirred at room temperature. After 5 h, the mixture was filtered and washed 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%-20% EtOAc/hexane) to give 1-(benzyloxy)-4,5-difluoro-2-(2-iodoethyl)benzene (630 mg, 1.684 mmol, 77% yield) as colorless viscous oil. 1H NMR (500 MHz, CDCl3) δ 7.50-7.34 (m, 6H), 7.00 (dd, J=10.3, 9.2 Hz, 1H), 6.77 (dd, J=12.0, 6.6 Hz, 1H), 5.06 (s, 2H), 3.37 (t, J=7.5 Hz, 2H), 3.21-3.15 (m, 2H).

1. stirringthe resulting mixture was stirred at room temperature
2. waitAfter 5 h
3. filtrationthe mixture was filtered
4. washwashed the solids with DCM
5. washThe filtrate was washed with aq Na2S2O3
6. dry with materialthe organic phase was dried (Na2SO4)
7. filtrationfiltered
8. concentrationconcentrated
9. customThe residue was purified by flash chromatography (Biotage; 0%-20% EtOAc/hexane)

ORD record

ord-4334f4e62a56481591befe4167b2ed20

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09273067B2