N-bromobutanimide → 1-(Bromomethyl)-2-fluoro-3-nitrobenzene

A stirred solution of 2-fluoro-1-methyl-3-nitrobenzene (15.80 g, 101.94 mmol) and N-bromosuccinimide (18.14 g, 101.94 mmol) in CCl4 (400 mL) was treated with benzoyl peroxide (0.37 g, 1.52 mmol). The mixture was heated at reflux temperature overnight and then cooled to room temperature. The reaction mixture was filtered, and the filtrate was evaporated to dryness under reduced pressure. The residue was dissolved in CH2Cl2 (100 mL) and filtered again. The filtrate was evaporated to dryness under reduced pressure, and the residue was purified by MPLC on silica gel using a mixture of EtOAc and hexane as eluent to give 1-(bromomethyl)-2-fluoro-3-nitrobenzene (8.11 g, 34%) as an off-white solid. 1H NMR (400 MHz, CDCl3): δ 8.02 (m, 1H), 7.71 (m, 1H), 7.30 (td, 1H, J=8.4, 1.6 Hz), 4.55 (d, 2H, J=1.6 Hz).

1. temperatureThe mixture was heated
2. temperatureat reflux temperature overnight
3. filtrationThe reaction mixture was filtered
4. customthe filtrate was evaporated to dryness under reduced pressure
5. dissolutionThe residue was dissolved in CH2Cl2 (100 mL)
6. filtrationfiltered again
7. customThe filtrate was evaporated to dryness under reduced pressure
8. customthe residue was purified by MPLC on silica gel using
9. additiona mixture of EtOAc and hexane as eluent

ORD record

ord-439a5abf1843461e9e6105561b001c82

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08080568B1