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

Temperature

0 °C

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).

1. stirringthe resulting mixture was stirred at room temp
2. waitAfter 16 h
3. filtrationthe mixture was filtered
4. washwashing 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%-100% EtOAc/hexane; 20 CV)

ORD record

ord-5780838f6c9e4c059cef5f5f32445851

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09273067B2