N-Iodosuccinimide → 1-Bromo-3-(3-fluoro-4-iodobutyl)-benzene

Temperature

0 °C

A solution of 0.245 gm (1.16 mmol) of 1-bromo-3-but-3-enylbenzene in CH2Cl2 at 0° C. was treated with 0.39 gm (1.74 mmol) of N-iodosuccinimide and 1.05 gm (1.74 mmol) of 50% wt/wt tetrabutylammoniumdihydrogen trifluoride in CH2Cl2, stirred at 0° C. for 2 h, warmed to room temperature over a 1 h period and poured into CH2Cl2. The resultant organic phase was washed sequentially with water and brine, dried over Na2SO4 and concentrated under reduced pressure. Chromatography of the concentrate on silica gel with a gradient of hexanes to 7.0% EtOAc-hexanes afforded 1-bromo-3-(3-fluoro-4-iodo-butyl)-benzene as an oil, 0.40 gm (50% yield); 1H NMR (400 MHz, CDCl3) δ: 2.03 (m, 2H), 2.74 (m, 2H), 3.29 (dd, 2H, J=5.4, 19.1 Hz), 4.47 (m, 1H), 7.12 (m, 2H), 7.32 (m, 2H).

1. temperaturewarmed to room temperature over a 1 h period
2. washThe resultant organic phase was washed sequentially with water and brine
3. dry with materialdried over Na2SO4
4. concentrationconcentrated under reduced pressure
5. concentrationChromatography of the concentrate on silica gel with a gradient of hexanes to 7.0% EtOAc-hexanes

ORD record

ord-c4495aa416a14ef38c76020ea2551afd

Source dataset

uspto-grants-2008_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07423158B2