N-bromobutanimide → 4-(Bromomethyl)-1-fluoro-2-iodobenzene

4-Fluoro-3-iodotoluene (50 g, 210 mMol), N-bromosuccinimide (37.7 g, 212 mMol) and 2,2′-azobis-(2-methylpropionitrile) (348 mg, 2.12 mMol) were dissolved in carbon tetrachloride (300 mL) under an atmosphere of dry N2. The mixture was heated to reflux for 4 hours and then cooled to ambient temperature. The mixture was concentrated under vacuum and triturated with Et2O. The filtrate was successively washed with water, aqueous saturated NaHCO3 and brine. The ether layer was dried over MgSO4, filtered and concentrated under vacuum to give a red oil. The oil was chromatographed on flash silica gel eluting with hexanes to give 33.8 g of the titled compound as a white solid.

1. temperatureThe mixture was heated
2. temperatureto reflux for 4 hours
3. concentrationThe mixture was concentrated under vacuum
4. customtriturated with Et2O
5. washThe filtrate was successively washed with water, aqueous saturated NaHCO3 and brine
6. dry with materialThe ether layer was dried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated under vacuum
9. customto give a red oil
10. customThe oil was chromatographed on flash silica gel eluting with hexanes

ORD record

ord-47808013bdee4e72aa7ec309018f45ed

Source dataset

uspto-grants-2003_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06579887B2